Toluene → HCID 57717686, compound

HRID 1984831Notes

Reaction equation

HRID 1984831 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:13][C:14]([C:16]2[N:17]=[CH:18][C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[C:21]([O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=2)[CH:20]=3)=[O:15])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[Cl:37][C:38]1[CH:39]=[C:40](B(O)O)[CH:41]=[CH:42][C:43]=1[F:44].[C:48]1(C)C=CC=CC=1>CCCCCC.C(OCC)(=O)C>[CH3:48][O:12][C:10](=[O:11])[C@@H:9]([NH:13][C:14]([C:16]1[N:17]=[CH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[C:21]([O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=1)[CH:20]=2)=[O:15])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([C:40]2[CH:41]=[CH:42][C:43]([F:44])=[C:38]([Cl:37])[CH:39]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 68867921HCID 68867921, compound

Product 1

HCID 57717686HCID 57717686, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

50 mg (0.089 mmol) of 3-(4-bromo-phenyl)-(2S)-{[7-(4-tert-butyl-phenoxy)-isoquinoline-3-carbonyl]-amino}-propionic acid was reacted with 31 mg (0.17 mmol) of 3-chloro-4-fluorophenylboronic acid in toluene as described in procedure D. Column chromatography using 8:2 hexane and ethyl acetate as an eluent gave 46 mg of title compound as a white solid.

Sources & evidence

ORD record
ord-4497833e2b52443ebc8e7f320cb1ace1
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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