Tetrahydrofuran → HCID 66657790, compound

HRID 420989Notes

Reaction equation

HRID 420989 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[C:15]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:28][CH:27]=1)=[C:16]([NH:22][C:23](=[O:25])[CH3:24])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][C:11]([C:38]1[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].C1COCC1>CO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH:15]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37]3)=[CH:28][CH:27]=1)[CH:16]([NH:22][C:23](=[O:25])[CH3:24])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][C:11]([C:38]1[CH:43]=[CH:42][C:41]([C:44]([F:46])([F:45])[F:47])=[CH:40][CH:39]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 66658135HCID 66658135, compound

Product 1

HCID 66657790HCID 66657790, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(2-Acetylamino-1-(4-cyclopentyloxyphenyl)-2-ethoxycarbonylvinyl)-5-(4-trifluoromethylphenyl)indole-2-carboxylic acid ethyl ester ('370 mg-, 0.58 mmol; see step (b) above) in MeOH (15 mL) and THF (115 mL) was hydrogenated (rt, 7 bar) over Pd—C (10%, 300 mg) for 6.5 h. The mixture was filtered through Celite® and concentrated to give sub-title compound. Yield 378 mg (1100%)

Workup

  1. custom(rt, 7 bar)
  2. customfor 6.5 h
  3. filtrationThe mixture was filtered through Celite®
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-40597c3c5f9e40d790c1724e6ffde244
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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