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[ CAS No. 399-96-2 ] {[proInfo.proName]}

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Chemical Structure| 399-96-2
Chemical Structure| 399-96-2
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Product Details of [ 399-96-2 ]

CAS No. :399-96-2 MDL No. :MFCD00671760
Formula : C6H6FNO Boiling Point : -
Linear Structure Formula :- InChI Key :MXJQJURZHQZLNN-UHFFFAOYSA-N
M.W : 127.12 Pubchem ID :2735918
Synonyms :

Safety of [ 399-96-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 399-96-2 ]

* 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.

  • Downstream synthetic route of [ 399-96-2 ]

[ 399-96-2 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 455-93-6 ]
  • [ 399-96-2 ]
  • 2
  • [ 399-96-2 ]
  • [ 81765-97-1 ]
  • [ 1335636-33-3 ]
YieldReaction ConditionsOperation in experiment
To the solution of 4-amino-2-fluorophenol (41 mg, 0.32 mmol) in dried DMF (3 mL), was added NaH (13 mg, 0.54 mmol). The mixture was stirred at 0 °C for 10 min, and then a solution of 4-chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine 4i (50 mg, 0.19 mmol) in dried DMF (1 mL) was added. The mixture was stirred at 0 °C for 1.5 h. Ice water (5 mL) was added to quench the reaction and the mixture was extracted by Et2O (3 .x. 10 mL). The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to obtain the crude product, which was purified by silica gel column chromatograph.
  • 3
  • [ 399-96-2 ]
  • [ 81765-97-1 ]
  • [ 1321618-91-0 ]
  • 4
  • [ 628-36-4 ]
  • [ 399-96-2 ]
  • [ 1339328-46-9 ]
YieldReaction ConditionsOperation in experiment
36.5% With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; toluene; at 120℃; for 3h;microwave irradiation; A mixture of 4-amino-2-fluorophenol (509 mg, 4.00 mmol), N-formylformohydrazide(426 mg, 4.84 mmol), and /?-toluenesulfonic acid (826 mg, 4.34 mmol) in toluene (15 mL) and DMF (1.5 mL) was heated under microwave irradiation at 120 °C for 3 h. The mixture was concentrated and the residue was partitioned between DCM and water. The organic phases were combined, dried over MgS04, filtered, and concentrated. The residue was purified by column chromatography (Si02, hexane/EtOAc gradient and then EtOAc/MeOH 10: 1) to give the title compound as a tan solid (262 mg, 36.5percent). Exact mass calculated for C8H6FN30: 179.05, found: LCMS mlz = 180.2 [M+H]+; lU NMR (400 MHz, DMSO- ) delta ppm 7.06-7.10 (m, 1H), 7.32- 7.35(m, 1H), 7.62-7.66 (m, 1H), 8.98 (s, 2H). 10.2 (s, 1H).
  • 5
  • [ 399-96-2 ]
  • [ 74420-05-6 ]
  • 3-fluoro-4-((1-methyl-1H-pyrrolo [2,3-b]pyridin-4-yl)oxy)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With sodium carbonate; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; water; at 80℃; General procedure: P-aminophenol or 2-fluoro-4-aminphenol 18a-b (0.1 mol)whichwas dissolved in tetrahydrofuran (50 ml),was added to a 1,4-dioxane/H2O(50 ml, 5:1) solution of compounds 17a-b or 20a-b,sodium carbonate and hydrogen sodium at 80 C for 2 h. Then thesolution was concentrated in vacuum and washed with water,filtered to give a solid.
  • 6
  • [ 399-96-2 ]
  • [ 100-39-0 ]
  • [ 168268-00-6 ]
YieldReaction ConditionsOperation in experiment
52% With potassium tert-butylate; In N,N-dimethyl-formamide; at 0℃; p-hydroxy-3-fluoroaniline (1.0 g, 7.87 mmol) was dissolved in 10 mL of anhydrous DMF, cooled to 0 C., then potassium tert-butoxide (0.88 g, 7.87 mmol) was added thereto, after stirring for 10 min, benzyl bromide (1.35 g, 7.87 mmol) was added therein, and the reaction was monitored by TLC. After the reaction is completed, the resultant was extracted with EA, then washed with saturated NaHCO3 and saturated brine, dried over anhydrous Na2SO4 and concentrated to give the crude compound 37, which was purified by column chromatography to give a colorless liquid, yield 52%. 1H NMR (CDCl3, 300 MHz): delta 7.41-7.28 (m, 5H), 6.91 (dd, 1H), 6.46 (dd, 1H), 6.32 (m, 1H), 4.97 (s, 2H), 4.98 (s, 2H).
  • 7
  • [ 399-96-2 ]
  • [ 13790-39-1 ]
  • [ 1201939-89-0 ]
YieldReaction ConditionsOperation in experiment
65% With sodium hydride; In dimethyl sulfoxide; at 80℃; for 1h;Inert atmosphere; Sodium hydride (60 mg, 2.5 mmol) was added to a mixture of 4-amino-2-fluorophenol (200mg, 1.6 mmol) and <strong>[13790-39-1]4-chloro-6,7-dimethoxyquinazoline</strong> (424 mg, 1.9 mmol) in DMSO (8 mL)under nitrogen. The resulting mixture was stirred at 80C for 1 hour, then concentrated. The5 crude product was purified by flash silica chromatography, elution gradient 1 to 10% methanolin DCM. Pure fractions were evaporated to dryness to afford the title compound as a black oil(320 mg, 65%). 1H NMR (DMSO-d6, 300 MHz) 8 3.99 (6H, d), 5.42 (2H, s), 6.33- 6.57 (2H,m), 7.06 (lH, t), 7.40 (lH, s), 7.54 (lH, s), 8.56 (lH, s); m/z: ES+ [M+H]+ 316.
64% To a solution of 4-amino-2-fluorophenol (17.8 g, 140 mmol, 1.4 eq) in DMF (200 mL) was added NaH (10 g, 250 mmol, 2.5 eq) at 0 C. The reaction was stirred at rt for 30 min and <strong>[13790-39-1]4-chloro-6,7-dimethoxyquinazoline</strong> (22.4 g, 100 mmol, 1.0 eq) was added to the mixture under stirring. The reaction solution was warmed to 90 C and stirred overnight. After cooling to room temperature, the reaction was quenched with saturated aqueous NH4Cl. The mixture was extracted with ethyl acetate (3×250 mL) twice. The combined organic layer was washed with brine (2×150 mL), dried over Na2SO4, concentrated in vacuo and further purified by flash chromatography on silica gel to get the product as a solid. (20.2 g, 64%). 1H NMR (400 MHz, d6-DMSO) δ 8.54 (s, 1H), 7.53 (s, 1H), 7.38 (s, 1H), 7.04 (t, J = 8.8 Hz, 1H), 6.50 (dd, J1 = 2.4 Hz, J2 = 12.8 Hz, 1H), 6.42 (dd, J1 = 2.0 Hz, J2 = 8.4 Hz, 1H), 5.38 (s, 2H), 3.98 (s, 3H) , 3.97 (s, 3H). HRMS (ESI) for C16H14FN3O3 [M+H]+, calcd: 316.1044, found: 316.1045.
9.1 g With N-ethyl-N,N-diisopropylamine; In ethyl acetate; at 20 - 60℃; for 2h; (1)Add 4-amino-2-fluorophenol (6.5g, 51mmol) to 100mLEthyl acetate,After stirring at room temperature, diisopropylethylamine (19.4 g, 150 mmol) was added.At the same time, the temperature is raised to 60 C, and <strong>[13790-39-1]4-chloro-6,7-dimethoxyquinazoline</strong> is added.(13.5 g, 60 mmol) of an ethyl acetate solution was slowly added to the above reaction solution.Stop the reaction after 2 hours.Extract twice with water, dry the ethyl acetate layer with anhydrous magnesium sulfate and spin dry4-(6,7-dimethoxyquinazolin-4-yloxy)-3-fluoroaniline(9.1g, 29mmol);
With potassium tert-butylate; In N,N-dimethyl-formamide; at 100℃; for 12h; General procedure: To a mixture of 1a (153 mg, 1 mmol, 1.0 eq), 4-amino-2-fluorophenol (127 mg ,1 mmol,1.0 eq), t-BuOK (336 mg, 3 mmol, 3.0 eq) in anhydrous DMF (5 mL). After stirring for 12 h at 100 C, then it was dilute of water (100 mL). The aqueous phase was extracted with ethyl acetate and dried over Na2SO4. The residue was purified using silica gel chromatography to give the intermediate 2a as a yellow solid (126.9 mg, 52% yield).
With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 0.333333h; A mixture of 4-chloro-6,7- dimethoxyquinazoline (225 mg, 1 mmol), 4-amino-2-fluorophenol (150 mg, 1.09 mmol) and Cs2CO3(500 mg, 1.52 mmol) in DMF (2 mL) was stirred at 80 C for 20 min and then cooled to room temperature. Water was added and the resulting suspension was filtered. The collected solid was washed with water and dried to give crude Compound QA2-1 (336 mg). MS for C16H14FN3O3: m/z 316 (MH+).

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