Boron tribromide → HCID 11342810, compound

HRID 2373803Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C@@H:16]([NH:23][C:24]([C:26]3[CH:27]=[C:28]([C:35]4[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[C:37]([C:45]([F:48])([F:47])[F:46])[CH:36]=4)[CH:29]=[CH:30][C:31]=3[O:32]CC)=[O:25])[C:17]3[O:21][N:20]=[C:19]([CH3:22])[N:18]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].B(Br)(Br)Br>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]([CH2:15][C@@H:16]([NH:23][C:24]([C:26]3[CH:27]=[C:28]([C:35]4[CH:36]=[C:37]([C:45]([F:46])([F:47])[F:48])[CH:38]=[C:39]([C:41]([F:43])([F:44])[F:42])[CH:40]=4)[CH:29]=[CH:30][C:31]=3[OH:32])=[O:25])[C:17]3[O:21][N:20]=[C:19]([CH3:22])[N:18]=3)=[CH:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 57717996HCID 57717996, compound

Product 1

HCID 11342810HCID 11342810, compoundYield 72.3%

Procedure

4-Hydroxy-3′,5′-bis-trifluoromethyl-biphenyl-3-carboxylic acid [2-(3′-chloro-4′-fluoro-biphenyl-4-yl)-1-(R)-(3-methyl-[1,2,4]oxadiazol-5-yl)-ethyl]-amide (48 mg) was prepared from 4-Ethoxy-3′,5′-bis-trifluoromethyl-biphenyl-3-carboxylic acid [2-(3′-chloro-4′-fluoro-biphenyl-4-yl)-1-(R)-(3-methyl-[1,2,4]oxadiazol-5-yl)-ethyl]-amide (69 mg, 0.10 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-ac04004a797744a8826f8d86439331d1
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459472B2

Reaction notes

Loading…