Sodium Hydroxide → 6-fluoro-3-(1H-pyrazol-4-yl)-1H-indole

HRID 2274826Notes

Reaction equation

F[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][CH:6]=[C:5]2[C:12]1[CH:13]=[N:14][N:15](CC2CCNCC2)[CH:16]=1.[OH-].[Na+]>CO.O>[F:11][C:10]1[CH:9]=[C:8]2[C:4]([C:5]([C:12]3[CH:16]=[N:15][NH:14][CH:13]=3)=[CH:6][NH:7]2)=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 6-fluoro-1-(phenylsulfonyl)-3-(1H-pyrazol-4-yl)-1H-indole (Intermediate 5; 183 mg; 0.54 mmol) in MeOH (20 mL) was added a solution of NaOH (142 mg; 3.55 mmol) in water (1 mL). The reaction mixture was stirred at 85° C. for 4 h, concentrated, diluted with H2O (5 mL), and extracted with Et2O (10 mL×3). The combined organic layers were washed with water (10 mL×2), brine (10 mL), dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by preparative HPLC. 39 mg (36%) of the title compound was obtained as a white solid.

Workup

concentrationconcentrated
additiondiluted with H2O (5 mL)
extractionextracted with Et2O (10 mL×3)
washThe combined organic layers were washed with water (10 mL×2), brine (10 mL)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-f81a60b24f9045a88e3d9de3a4d6e381
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126984B2

Reaction notes

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