Styrylboronic acid → 2-(2-Chlorophenylamino)-3,4-difluoro-6-styrylbenzoic acid methyl ester

HRID 1723690Notes

Reaction equation

[C:1]1(/[CH:7]=[CH:8]/B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:12][O:13][C:14](=[O:32])[C:15]1[C:20](Br)=[CH:19][C:18]([F:22])=[C:17]([F:23])[C:16]=1[NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31]>COCCOC.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][O:13][C:14](=[O:32])[C:15]1[C:20]([CH:8]=[CH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:19][C:18]([F:22])=[C:17]([F:23])[C:16]=1[NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31]

Participants

Conditions

Temperature: 90 °C

Procedure

Pd(PPh3)4 (0.313 g, 0.271 mmol) and trans-2-phenylvinylboronic acid (1.105 g, 7.468 mmol) were added to a mixture of 6-bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester (2.00 g, 5.31 mmol) in 35 mL DME and 8 mL 2.0 M aqueous K2CO3 solution. The reaction mixture was heated under a N2 atmosphere to 90° C. and stirred for 16 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and water and the layers separated. The organic layer was dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography gave 1.20 g (56%) clean desired product.

Workup

temperatureAfter cooling to room temperature
customthe layers separated
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated under reduced pressure
customPurification by flash column chromatography

Sources & evidence

ORD record: ord-e9463b7a768b4218b3cdeeb8eb326977
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07485643B2

Reaction notes

Loading…