3-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride) → HCID 10480005, compound

HRID 1245089Notes

Reaction equation

HRID 1245089 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5](OCCCCCCC)=[C:6]([CH:38]=1)[C:7]([NH:9][C@@H:10]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2OC2C=CC(C(F)(F)F)=CC=2)=[CH:17][CH:16]=1)[C:11]([OH:13])=[O:12])=[O:8].[Cl:47][C:48]1[CH:49]=[C:50](B(O)O)[CH:51]=[CH:52][C:53]=1[F:54]>>[C:18]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:17]=[CH:16][C:15]([CH2:14][C@H:10]([NH:9][C:7]([C:6]2[CH:38]=[CH:2][C:3]([C:50]3[CH:51]=[CH:52][C:53]([F:54])=[C:48]([Cl:47])[CH:49]=3)=[CH:4][CH:5]=2)=[O:8])[C:11]([OH:13])=[O:12])=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 58717681HCID 58717681, compound

Product 1

HCID 10480005HCID 10480005, compoundYield 81.6%

Procedure

3-Biphenyl-4-yl-(2S)-[(5-bromo-benzoyl-amino)-propionic acid (100 mg, 0.23 mmol) was reacted with 3-chloro-4-fluoro-phenyl boronic acid (0.123 mg, 0.69 mmol) by following general procedure D to afford title compound (89 mg, 80%) as a white solid. 1H NMR (400 MHz, CD3COCD3): 4.05 (dd, 2H), 5.00 (m, 1H), 7.32 (m, 1H), 7.44 (m, 4H), 7.62 (m, 4H), 7.71 (m, 1H), 7.74 (m, 2H), 7.84 (m, 1H), 7.96 (m, 3H). LC/MS (m/z): 474 (M+1)+.

Sources & evidence

ORD record
ord-c9e7ee95d0004d96b9e87c0f5e86abd0
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

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