[ CAS No. 661463-17-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 661463-17-8 * Storage: {[proInfo.prStorage]}

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	Inquiry	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price) ]}	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ item.pr_usastock ]}		{[ item.pr_chinastock ]}	{[ item.pr_remark ]}	Login		Inquiry

Please Login or Create an Account to: See VIP prices and availability

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

For Research Only 120K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 661463-17-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 661463-17-8 ]

SDS Specification

Alternatived Products of [ 661463-17-8 ]

Product Details of [ 661463-17-8 ]

CAS No. :	661463-17-8	MDL No. :	MFCD09261094
Formula :	C₉H₅BrFN	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	HIWPTYUKGHNQCU-UHFFFAOYSA-N
M.W :	226.05	Pubchem ID :	17976318
Synonyms :

Calculated chemistry of [ 661463-17-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	49.4
TPSA :	12.89 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.56 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.18
Log Po/w (XLOGP3) :	2.98
Log Po/w (WLOGP) :	3.56
Log Po/w (MLOGP) :	2.98
Log Po/w (SILICOS-IT) :	3.54
Consensus Log Po/w :	3.05

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.74
Solubility :	0.0416 mg/ml ; 0.000184 mol/l
Class :	Soluble
Log S (Ali) :	-2.91
Solubility :	0.275 mg/ml ; 0.00122 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.84
Solubility :	0.00327 mg/ml ; 0.0000145 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.62

Safety of [ 661463-17-8 ]

Signal Word:	Danger	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H302-H318	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 661463-17-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 661463-17-8 ]
Downstream synthetic route of [ 661463-17-8 ]

[ 661463-17-8 ] Synthesis Path-Upstream 1~3

1
[ 391-78-6 ]
[ 661463-17-8 ]

Yield	Reaction Conditions	Operation in experiment
79%	With phosphorus tribromide In N,N-dimethyl-formamide at 45 - 60℃; for 0.75 h;	To a solution of intermediate A.i (20 g, 122.58 mmol) in DMF (130 niL), heated to 60⁰C, was added phosphorous tribromide (13 mL, 1.15 eq.). The reaction was heated at 45°C for 45 min. After cooling to rt, the reaction was diluted with water (200 mL). Sat. Na₂CO₃ was added until pH 10 was reached. The solid was formed was filtered off. The solid was taken up in EA (200 mL) and the solution was concentrated to dryness. The residue was chromatographed (EA) to afford the title bromide as a yellowish solid (22 g, 79percent yield). ¹H NMR (CDCl₃) δ: 8.70 (d, J = 4.7 Hz, IH); 8.14 (m, IH); 7.96 (d, J = 4.7 Hz, IH); 7.81-7.73 (m, 2H).

Reference： [1] Patent: WO2008/152603, 2008, A1, . Location in patent: Page/Page column 36
[2] Patent: WO2017/21319, 2017, A1, . Location in patent: Page/Page column 32

2
[ 21873-50-7 ]
[ 661463-17-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	With phosphorus tribromide In DMF (N,N-dimethyl-formamide); water at 0 - 20℃; for 1.08333 h;	To a solution of (10b) (11.3 g, 69.3 mmol) in DMF (350 ml) was added dropwisephosphorous tribromide (7.1 ml, 76.3 mmol) over five minutes (slightly exothermic). The reaction was allowed to cool to room temperature and was then diluted with ice water and stirred 1 hour then diluted with additional water. The product was filtered off, washed with water and dried in vacuo to afford the product as a white solid (12.0 g, 76percent). MS (+ve ion electrospray) m/z 226 (MH+).

Reference： [1] Patent: WO2004/14361, 2004, A1, . Location in patent: Page/Page column 41

3
[ 371-40-4 ]
[ 661463-17-8 ]

Reference： [1] Patent: WO2017/21319, 2017, A1,
[2] Patent: WO2008/152603, 2008, A1,

[ 661463-17-8 ] Synthesis Path-Downstream 1~10

1
[ 21873-50-7 ]
[ 661463-17-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	With phosphorus tribromide; In DMF (N,N-dimethyl-formamide); water; at 0 - 20℃; for 1.08333h;	To a solution of (10b) (11.3 g, 69.3 mmol) in DMF (350 ml) was added dropwisephosphorous tribromide (7.1 ml, 76.3 mmol) over five minutes (slightly exothermic). The reaction was allowed to cool to room temperature and was then diluted with ice water and stirred 1 hour then diluted with additional water. The product was filtered off, washed with water and dried in vacuo to afford the product as a white solid (12.0 g, 76%). MS (+ve ion electrospray) m/z 226 (MH+).

Reference： [1]Patent: WO2004/14361,2004,A1 .Location in patent: Page/Page column 41

2
[ 661463-17-8 ]
[ 6783-05-7 ]
[ 1093219-05-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃;	To a hot (100 0C) solution of intermediate A.ii (18.5 g, 81.8 mmol), K2CO3 (14.7 g, 106 mmol), trans-2-phenylboronic acid (13.7 g, 90 mmol) in dioxane (320 mL) and water (80 mL) was added Pd(PPh3 )4 (4.77 g, 5 mol%). The resulting mixture was stirred at 1000C over night. After cooling, the reaction mixture was diluted with water (300 mL). The volatiles were removed in vacuo and the residue was taken up in EA (300 mL). The two layers were separated and the aq. layer was extracted one more with EA (300 mL). The combined org. layers were washed with brine, dried over MgSO4, filtered and <n="39"/>concentrated to dryness. The residue was chromatographed (EA-Hept 1 :2) to afford the title compound as a yellow solid (17.79 g, 87% yield).1H NMR (CDCl3) delta: 8.89 (d, J = 4.6 Hz, IH); 8.16 (dd, J = 9.5, 5.5 Hz, IH); 7.83 (dd, J = 2.7, 9.5 Hz, IH); 7.70-7.63 (m, 4H); 7.55-7.34 (m, 5H).

Reference： [1]Patent: WO2008/152603,2008,A1 .Location in patent: Page/Page column 36-37

3
[ 391-78-6 ]
[ 661463-17-8 ]

Yield	Reaction Conditions	Operation in experiment
79%	With phosphorus tribromide; In N,N-dimethyl-formamide; at 45 - 60℃; for 0.75h;	To a solution of intermediate A.i (20 g, 122.58 mmol) in DMF (130 niL), heated to 600C, was added phosphorous tribromide (13 mL, 1.15 eq.). The reaction was heated at 45°C for 45 min. After cooling to rt, the reaction was diluted with water (200 mL). Sat. Na2CO3 was added until pH 10 was reached. The solid was formed was filtered off. The solid was taken up in EA (200 mL) and the solution was concentrated to dryness. The residue was chromatographed (EA) to afford the title bromide as a yellowish solid (22 g, 79percent yield). 1H NMR (CDCl3) delta: 8.70 (d, J = 4.7 Hz, IH); 8.14 (m, IH); 7.96 (d, J = 4.7 Hz, IH); 7.81-7.73 (m, 2H).
	With phosphorus tribromide; In N,N-dimethyl-formamide; at 45 - 60℃; for 0.75h;	To a solution of AMI0015 (2.30 g, 14.1 mmol, 1 equiv) in N,N-dimethylformamide (20 mL) at 60 °C was added phosphorus tribromide (1.52 mL, 16.2 mmol, 1.2 equiv). The mixture was cooled to 45 °C for 45 mins. After cooling to room temperature, the reaction was diluted with water (25 mL) and the pH was adjusted to ~ 10 with saturated aqueous NaHCCte. The resulting solid was washed in water, filtered and taken up in EtOAc and concentrated in vacuo, to afford 4-bromo-6-fluoroquinoline (3.12 g, 13.8 mmol, 98percent). The analyses were consistent with the data reported in the literature. Ref: WO2010/152603 (2008) TLC Rf 0.64 (EtOAc/MeOH 8:2) FontWeight="Bold" FontSize="10" H MR (400MHZ, DMSO-de) delta (ppm) 8.73 (d, J=4.6 Hz, 1H, NCH), 8.18 (m, 1H, NCCH), 8.00 (d, J=4.6 Hz, 1H, BrCCH), 7.77-7.88 (m, 2H, FCCH, FCCH) ppm 13CNMR (101 MHz, DMSO-de) delta (ppm) 162.5 (5), 150.5 (10), 146.0 (2), 133.5 (6), 128.6 (7), 128.5 (4), 126.6 (1), 121.2 (8), 1 10.5 (3) ppm IR (neat) v max 1585 (m) cm"1 LCMS (ESI+) m/z 227.0 [M79Br+H]+, 229.0 [M81Br+H]+ 11 RMS (ESI+) m/z calcd. 225.9662 m/z meas. 225.9962 [M+H]+

Reference： [1]Patent: WO2008/152603,2008,A1 .Location in patent: Page/Page column 36
[2]Patent: WO2017/21319,2017,A1 .Location in patent: Page/Page column 32

4
[ 661463-17-8 ]
[ 31180-85-5 ]
ethyl 2-(4-(6-fluoroquinolin-4-yl)-4-hydroxycyclohexyl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%		To a solution of <strong>[661463-17-8]4-bromo-6-fluoroquinoline</strong> (163 mg, 0.721 mmol) in THF (5 mL) at -78C was added t-BuLi (1.7M-3.2M in Heptane) (0.849 mL, 1.443 mmol) drop wise. It turned from clear to dark brown color. The reaction was stirred at -78C for 3 min. Then ethyl 2-(4-oxocyclohexyl) propanoate (130 mg, 0.656 mmol) in THF (1 mL) was added drop wise. The reaction was stirred at -78C for lh. The reaction was diluted with saturated NH4C1 and EtOAc. Organic was separated and washed with brine, dried over MgS04, filtered and concentrated to give a crude material. This material was purified with ISCO 40g, 40 mL/min. 0-100% EtOAc/Hexane in 35 min. The desired product was eluted with 55% EtOAc/Hexane to give 234A (100 mg, 0.290 mmol, 44%) as the mixture of the diastereomers.

Reference： [1]Patent: WO2016/73770,2016,A1 .Location in patent: Paragraph 0503

5
[ 371-40-4 ]
[ 661463-17-8 ]