Ethyl trans-crotonate → 3-[4-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-indol-1-yl]-butyric acid

HRID 551518Notes

Reaction equation

HRID 551518 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:25]=[C:24]4[C:20]([CH:21]=[CH:22][N:23]4[CH:26]([CH3:31])[CH2:27][C:28]([OH:30])=[O:29])=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)=[C:4]([O:32][CH3:33])[CH:3]=1.FC1C(F)=CC(C2C=CC(OCC3C=CC=C4C=3C=CN4)=CC=2)=C(OC)C=1.C(OC(=O)/C=C/C)C>>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[C:24]4[C:25]=3[CH:21]=[CH:22][N:23]4[CH:26]([CH3:31])[CH2:27][C:28]([OH:30])=[O:29])=[CH:13][CH:14]=2)=[C:4]([O:32][CH3:33])[CH:3]=1

Participants

4

Reactant 3

HCID 429065Ethyl trans-crotonateHCID 529397413-[6-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-indol-1-yl]-butyric acidHCID 529397424-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-1H-indole

Product 1

HCID 529398653-[4-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-indol-1-yl]-butyric acid

Procedure

3-[4-(4′,5′-Difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-indol-1-yl]-butyric acid was synthesized by a procedure similar to 3-[6-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-indol-1-yl]-butyric acid from starting materials 4-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-1H-indole and (E)-but-2-enoic acid ethyl ester to yield the product as a clear to opaque oil/film (6 mg, 13%). LC-MS (ES) calculated for C26H23F2NO4, 451.2; found m/z 452 [M+H]+.

Sources & evidence

ORD record
ord-61fcac5296d046dca4cc18d7023f5e61
Source dataset
uspto-grants-2011_05
Patent number
US07947728B1

Reaction notes

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