Sodium Carbonate → HCID 178517313, compound

HRID 1845967Notes

Reaction equation

C(O[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1B(O)O)=[O:5])C.Br[C:16]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:17]=1[NH2:18].C([O-])(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(O)C>[F:23][C:20]1[CH:21]=[CH:22][C:16]2[C:17]([CH:19]=1)=[N:18][C:4]([OH:5])=[C:6]1[C:7]=2[CH:8]=[CH:9][CH:10]=[CH:11]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-(ethoxycarbonyl)phenylboronic acid (7.0 g, 39 mmol), 2-bromo-5-fluoroaniline (7.4 g, 39 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (S-Phos, 0.32 g, 0.78 mmol), sodium acetate (4.1 g, 39 mmol), and palladium acetate (0.087 g, 0.39 mmol) in 18 ml. of ethanol was heated with stirring at 80° C. for 18 h. Additional 2-(ethoxycarbonyl)phenylboronic acid (2.0 g), S-Phos (0.095 g), palladium acetate (0.020 g), and sodium carbonate (1.2 g) was added and the mixture was stirred for 18 h. The solvent was removed by evaporation under reduced pressure, and the resulting solid was isolated by vacuum filtration, washing the remaining solid with water and then hexane. The remaining solid and dried in vacuo @50° C. to provide the title compound (4.39 g, 53% yield) which was used without further purification.

Workup

stirringthe mixture was stirred for 18 h
customThe solvent was removed by evaporation under reduced pressure
customthe resulting solid was isolated by vacuum filtration
washwashing the remaining solid with water
customThe remaining solid and dried in vacuo @50° C.

Sources & evidence

ORD record: ord-0fba0a1744804e45bcbf3c1d6c59941c
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08951964B2

Reaction notes

Loading…