6-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-indole-1-carboxylic acid tert-butyl ester → 6-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-1H-indole

HRID 551502Notes

Reaction equation

HRID 551502 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:26]=4[O:33][CH3:34])=[CH:21][CH:20]=3)[CH:15]=2)[CH:10]=[CH:9]1)=O)(C)(C)C>CO>[F:32][C:28]1[C:29]([F:31])=[CH:30][C:25]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH2:17][C:14]3[CH:15]=[C:16]4[C:11]([CH:10]=[CH:9][NH:8]4)=[CH:12][CH:13]=3)=[CH:20][CH:21]=2)=[C:26]([O:33][CH3:34])[CH:27]=1

Participants

3

Reactant 1

HCID 671519286-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 529398626-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-1H-indoleYield 100.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 6-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-indole-1-carboxylic acid tert-butyl ester (232 mg, 0.5 mmol) was added methanol and the mixture was microwaved at 150° C. for 30 min. The reaction was concentrated and dried from dichloromethane to yield 6-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-1H-indole as a white solid (184 mg, 99%). LC-MS (ES) calculated for C22H17F2NO2, 365.2; found m/z 366 [M+H]+.

Workup

  1. customthe mixture was microwaved at 150° C. for 30 min
  2. concentrationThe reaction was concentrated
  3. dry with materialdried from dichloromethane

Sources & evidence

ORD record
ord-5a7b4bf0d6944503a8e831b167af673c
Source dataset
uspto-grants-2011_05
Patent number
US07947728B1

Reaction notes

Loading…