Boron tribromide → HCID 11330971, compound

HRID 2373825Notes

Reaction equation

[C:1]1([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH:15][C:16]([C:18]2[CH:19]=[C:20]([C:32]3[CH:37]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:35]=[C:34]([C:42]([F:45])([F:44])[F:43])[CH:33]=3)[CH:21]=[CH:22][C:23]=2[O:24]CC2C=CC=CC=2)=[O:17])[C:9]2[O:13][N:12]=[C:11]([CH3:14])[N:10]=2)=[CH:3][CH:2]=1.B(Br)(Br)Br>>[C:1]1([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:2]=[CH:3][C:4]([CH2:7][C@@H:8]([NH:15][C:16]([C:18]2[CH:19]=[C:20]([C:32]3[CH:33]=[C:34]([C:42]([F:43])([F:44])[F:45])[CH:35]=[C:36]([C:38]([F:40])([F:41])[F:39])[CH:37]=3)[CH:21]=[CH:22][C:23]=2[OH:24])=[O:17])[C:9]2[O:13][N:12]=[C:11]([CH3:14])[N:10]=2)=[CH:5][CH:6]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 86597151HCID 86597151, compound

Product 1

HCID 11330971HCID 11330971, compoundYield 86.7%

Procedure

4-Hydroxy-3′,5′-bis-trifluoromethyl-biphenyl-3-carboxylic acid [2-biphenyl-4-yl-1-(R)-(3-methyl-[1,2,4]oxadiazol-5-yl)-ethyl]-amide (53 mg) was prepared from 4-benzyloxy-3′,5′-bis-trifluoromethyl-biphenyl-3-carboxylic acid [2-biphenyl-4-yl-1-(R)-(3-methyl-[1,2,4]oxadiazol-5-yl)-ethyl]-amide (70 mg, 0.1 mmol) and boron tribromide (0.25 mL, 0.25 mmol, 1.0 M solution in DCM) following the general procedure P.

Sources & evidence

ORD record: ord-6867bed59c1a4c66be9ae5a8be65a52a
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459472B2

Reaction notes

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