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

HRID 551510Notes

Reaction equation

HRID 551510 reaction equation
C(OC(N1C2C(=CC=C([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)C=2)C=C1)=O)(C)(C)C.[C:35]([O:39][C:40]([N:42]1[C:50]2[C:45](=[C:46](CO)[CH:47]=[CH:48][CH:49]=2)[CH:44]=[CH:43]1)=[O:41])([CH3:38])([CH3:37])[CH3:36].FC1C(F)=CC(C2C=CC(O)=CC=2)=C(OC)C=1>>[C:35]([O:39][C:40]([N:42]1[C:50]2[C:45](=[C:46]([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:47]=[CH:48][CH:49]=2)[CH:44]=[CH:43]1)=[O:41])([CH3:38])([CH3:36])[CH3:37]

Participants

4

Reactant 3

HCID 12148524tert-Butyl 4-(hydroxymethyl)-1H-indole-1-carboxylateHCID 582599934',5'-Difluoro-2'-methoxy-biphenyl-4-olHCID 671519286-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 671519404-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-indole-1-carboxylic acid tert-butyl ester

Procedure

4-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-indole-1-carboxylic acid tert-butyl ester was synthesized by a procedure similar to 6-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-indole-1-carboxylic acid tert-butyl ester from starting materials 4-hydroxymethyl-indole-1-carboxylic acid tert-butyl ester and 4′,5′-difluoro-2′-methoxy-biphenyl-4-ol to yield the product as a white solid (880 mg, 70%). LC-MS (ES) calculated for C27H25F2NO2, 465.2; found m/z 466 [M+H]+.

Sources & evidence

ORD record
ord-029ee07459fc47be845ada8c010993b9
Source dataset
uspto-grants-2011_05
Patent number
US07947728B1

Reaction notes

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