Tetrahydrofuran → HCID 16051656, compound

HRID 2235102Notes

Reaction equation

HRID 2235102 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:41])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH:24]=[C:23]3[C:19]([CH2:20][CH2:21][N:22]3[S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=3)(=[O:27])=[O:26])=[C:18]([O:38][CH3:39])[CH:17]=2)=[O:15])=[CH:9][C:8]=1[F:40])C.O1CCCC1>CO>[F:40][C:8]1[CH:9]=[C:10]([NH:13][C:14]([C:16]2[CH:24]=[C:23]3[C:19]([CH2:20][CH2:21][N:22]3[S:25]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:35])([F:37])[F:36])[CH:29]=3)(=[O:26])=[O:27])=[C:18]([O:38][CH3:39])[CH:17]=2)=[O:15])[CH:11]=[CH:12][C:7]=1[C:6]([OH:41])=[O:5]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 68698353HCID 68698353, compound

Product 1

HCID 16051656HCID 16051656, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 3 N aqueous KOH solution (2 mL) was added to a solution of 2-fluoro-4-{[4-methoxy-1-(3-trifluoromethyl-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid ethyl ester (14.4 mg, 0.03 mmol, 1 equiv.) in 2:1 tetrahydrofuran:methanol (3 mL) and the mixture was shaken for 16 hours. The mixture was concentrated under a stream of N2 and the pH adjusted to 1 with 3 N aqueous HCl solution (2 mL). The mixture was extracted with 1:1 CHCl3:IPA (3×1 mL). The organic layers were combined, dried over Na2SO4 and the solvent was removed under reduced pressure to afford 2-fluoro-4-{[4-methoxy-1-(3-trifluoromethyl-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid, 12 mg (86% yield). LC @215 nm; Rt 2.27: 98%, m/z (ES+): 539 (M+H+.); δH (400 MHz; d6-Acetone) 10.69 (1H, br. s), 8.03 (2H, m), 7.90 (1H, d), 7.86-7.81 (3H, m), 7.82-7.72 (2H, m), 7.50 (1H, d), 7.21 (1H, s), 3.98 (2H, t), 3.74 (3H, s), 2.82 (2H, t).

Workup

  1. concentrationThe mixture was concentrated under a stream of N2
  2. extractionThe mixture was extracted with 1:1 CHCl3
  3. dry with materialdried over Na2SO4
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cced9db1793d4d72a5e82b741e18db32
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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