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CAS No. : | 885521-46-0 | MDL No. : | MFCD07781585 |
Formula : | C8H5IN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DYZNTIADYAHDQK-UHFFFAOYSA-N |
M.W : | 288.04 | Pubchem ID : | 24728200 |
Synonyms : |
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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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 120℃; for 6h;Sealed; Microwave irradiation; | Method C (Suzuki-Miyaura cross coupling)A mixture of 3-iodo-lH-indazole (1.0 equiv), 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)benzenesulfonamide (1.2 equiv), base and palladium catalyst (0.05 equiv) in solvents was degassed with Ar and heated sealed in a Biotage microwave reactor. The crude material after filtration through Celite using MeOH to rinse the pad. In the majority of examples, purification by preparative HPLC provided the target material.To a mixture of arylboronic acid (5 mmol) and glyoxylic acid monohydrate (460 mg, 5 mmol) in CH2CI2 (25 mL) was added dialkylamine (5 mmol). The resulting mixture was stirred overnight at rt. After evaporation of solvents, it was used as crude or purified by column chromatography.Synthesis of 3-(3-(methylsulfonyl)phenyl)-lH-indazole-5-carboxylic acidThe title compound was synthesized according to the General Method C, utilizing 3-iodo- lH-indazole-5-carboxylic acid (1.002 g, 3.47 mmol), (3-(methylsulfonyl)phenyl)boronic acid-68-4820V.1 (891.7 mg, 4.46 mmol), Pd(PPh3)4 (107.0 mg, 0.093 mmol), toluene (7 mL), EtOH (7 mL), and saturated aqueous Na2C03 (3.5 mL). The degassed solution was sealed and heated in a microwave reactor at 120 C for 6 h. After cooling to room temperature, the mixture was diluted with Et20 (300 mL) and acidified with aqueous HC1 (1M, 25 mL) and water (50 mL).Undissolved solid was collected by filtration and rinsed with water (10 mL) and 25% EtOH / Et20 (10 mL). The separated Et20 layer was discarded since it contained only traces of product. The wet solid was transferred using a mixture of acetone, THF and DMF, and evaporated in vacuo. MeOH in Et20 (50%, 10 mL) was added and the suspension was sonicated, and filtered. The solid was rinsed with MeOH in Et20 (50%, 10 mL) to provide the title compound as an pale grey solid (946.1 mg, 86 %). NMR (400 MHz, DMSO-d6) 8 ppm 13.79 (s, 1 H), 12.95 (br.s, 1H), 8.68 (s, 1 H), 8.47 (s, 1 H), 8.35 (d, J=8.0 Hz, 1 H), 8.00 (d, J=8.5 Hz, 2 H), 7.86 (t, J=8.0 Hz, 1 H), 7.71 (d, J=9.3 Hz, 1 H), 3.31 (s, 3 H); MS ESI 317.2 [M + H]+, calcd for [Ci5H12N204S + H]+ 317.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0℃; for 1h; | The mixture of 1-cyclohexylpropan-l -amine (380 mg, 2.69 mmol), 3- iodo-lH-indazole-5-carboxylic acid (774.9 mg, 2.69 mmol), DIPEA (1.33 mL, 8.07 mmols) in DMF (8 mL) was cooled down to 0C and added TBTU (864 mg, 2.69 mmol). After stirring at 0 C for 1 h, H20 was added followed by EtOAc. The organic layer was separated and washed with H20 (3x),brine, dried over Na2S04 and concentrated under reduced pressure to provide the title compound as a light yellow solid (418 mg, 38 % yield). ? NMR (400 MHz, CDCli) delta ppm 10.65 (s, 1H), 7.92 (m, 2H), 7.54 (d, J = 8.8 Hz, 1H), 5.89 (d, J = 4.1 Hz, 1H), 4.02 (m, 1H), 1.86-1.67 (m, 6H), 1.56-1.44 (m, 2H), 1.31-1.06 (m, 4H), 0.99 (t, J= 8.2 Hz, 3H); MS ESI [M + H]+412.3, calcd for [C17H22I 3O+ H]+ 412.09. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 24℃; | The title compound was synthesized according to General Method A utili?3-iodo-lH-indazole-5-carboxylic acid (358 mg, 1.23 mmol), (S)- cyclopropyl(2-fluorophenyl) methanamine hydrochloride (250 mg, 1.23 mmol), BOP-C1 (576 mg, 1.3 mmol), DIPEA (1.08 mL, 6.19 mmol) and DMF (5 mL) at 0C. The reaction was stirred and slowly warmed to rt and stirred at 24C for 3 h. The reaction was concentrated and purified by flash chromatography (Biotage isolera 60 g C 18-HS , 5-90% MeOH in 0.1% TFA.H20) to give the title compound as an off white solid (405 mg, 75%). ? NMR (400 MHz, CD3OD) delta ppm 8.08 (s, 1 H), 7.95 (dd, J=8.8, 1.6 Hz, 1 H), 7.56-7.58 (m, 2 H), 7.26-7.31 (m, 1 H), 7.17 (t, J=7.6 Hz, 1 H), 7.09 (t, J=10 Hz, 1 H), 4.76 (d, J=9.2 Hz, 1 H), 1.41-1.50 (m, 1 H), 0.66-0.72 (m, 1 H), 0.58-0.62 (m, 1 H), 0.50-0.56 (m, 2 H); MS ESI 436.2 [M + H]+, calcd for[C18Hl5FP 30+H]+ 436. |
75% | With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 24℃; for 3h; | Synthesis of (S)-N-(cvcloprovyl(2-fluorophenyl)methyl)-3-iodo-lH-indazole-5-carboxamide The title compound was synthesized according to General Method A utilizing 3- iodo-lH-indazole-5-carboxylic acid (358 mg, 1.23 mmol), (S)-cyclopropyl(2- fluorophenyl) methanamine hydrochloride (250 mg, 1.23 mmol), BOP-C1 (576 mg, 1.3 mmol), DIPEA (1.08 mL, 6.19 mmol) and DMF (5 mL) at 0C. The reaction was stirred and slowly warmed to rt and stirred at 24C for 3 h. The reaction was concentrated and purified by flash chromatography (Biotage isolera 60 g C18-HS . 5-90% MeOH in 0.1% TFA.H20) to give the title compound as an off white solid (405 mg, 75%). NMR (400 MHz, CD3OD) 8 ppm 8.08 (s, 1 H), 7.95 (dd, .7=8.8, 1.6 Hz, 1 H), 7.56-7.58 (m, 2 H), 7.26-7.31 (m, 1 H), 7.17 (t, .7=7.6 Hz, 1 H), 7.09 (t, J=10 Hz, 1 H), 4.76 (d, .7=9.2 Hz, 1 H), 1.41-1.50 (m, 1 H), 0.66-0.72 (m, 1 H), 0.58-0.62 (m, 1 H), 0.50-0.56 (m, 2 H); MS ESI 436.2 [M + H]+, calcd for [C18H,5FrN30+H]+ 436. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | -iodo-lH-indazole-5-carboxylic acid (1.73 g, 6.00 mmol), isobutyl chloroformate (1.57 mL, 12.0 mmol), DIPEA (2.09 mL, 1.80 mmol), and DMF (20 mL) were combined and cooled to 0 C. The reaction was stirred at 0 C for 10 min at which point 2,2,2-trifluoro-l-phenylethanamine (1.27 mg, 6.00 mmol) was added. The mixture was warmed to rt and stirred for 1.5 h, The crude reaction was subsequently diluted with EtOAc and washed with aq NaHC03 and brine. The mixture was dried over MgS04 and the solvent was removed under reduced pressure to give the title compound as a beige solid (1.45 g, 44%). The product was used without further purification. MS ESI 546.1 [M + H]+, calcd for [C21H19F3I 303 + H]+ 546.0 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0℃; for 1h; | N-(Cyclopropyl(thiazol-2-yl)methyl)-3-iodo-1H-indazole-5-carboxamide The title compound was synthesized according to General Method A utilizing <strong>[885521-46-0]3-iodo-1H-indazole-5-carboxylic acid</strong> (255 mg, 0.88 mmol), cyclopropyl(thiazol-2-yl)methanamine (150 mg, 0.97 mmol), TBTU (310 mg, 0.97 mmol), DIPEA (0.31 mL, 1.8 mmol), and DMF (8 mL). The reaction was stirred at 0 C. for 1 h. The crude reaction was subsequently diluted with H2O. A filtration and washing (H2O) of the precipitate provided the desired product as a beige solid (195 mg, 52%). The product used without further purification. 1H NMR (400 MHz, CD3OD) delta ppm 8.16 (br. s., 1H), 7.99 (m., 1H), 7.77 (br. s., 1H), 7.46-7.67 (m, 2H), 1.45-1.68 (m, 1 H), 0.46-0.90 (m, 4H); MS ESI 425.0 [M+H]+, calcd for [C15H13IN4OS+H]+ 425.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25℃; for 12h; | D. N-(l-(2-chlorophenyl)-2-methylpropyl)-3-iodo-lH-indazole-5-carboxamide The title compound was synthesized according to General Method A by using l-(2-chlorophenyl)-2- methylpropan-1 -amine (0.55 g, 2.99 mmol), DMF (11 mL), 3-iodo-lH-indazole-5-carboxylic acid (863 mg, 2.99 mmol), DIPEA (2.09 mL, 11.98 mmol) and TBTU (960 mg, 2.99 mmol). The resultant reaction mass stirred at 25C for 12 h and then quenched it in 0 (440 mL). The solid collected by filtration and was washed with H20 to provide the title compound (cream color solid, 1.29 g, 95%). NMR (400 MHz, DMSO-d6) delta 13.76 (s, 1H), 8.91 (d, .7=8.8 Hz, 1H), 7.91 (d, J=9.2 Hz, 1H), 7.74- 7.66 (m, 1H), 7.59 (d, J=8.8 Hz, 1H), 7.46-7.22 (m, 4H), 5.27 (t, J=9.2 Hz, 1H),2.20-2.15 (m, 1H), 1.08 (d, .7=6.0 Hz, 3H), 0.79 (d, J=6.8 Hz, 3H) ; MS ESI 454 [M + H]+, calcd for [Cl8H17CHN30 + H]+ 454. |
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