Sodium Carbonate → HCID 21905279, compound

HRID 1247397Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH:9]([O:22][CH3:23])[C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)=[O:11])=[C:4]([F:24])[CH:3]=1.[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.CCO.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:20]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][NH:12][C:10](=[O:11])[CH:9]([C:5]2[C:6]([F:8])=[CH:7][C:2]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:3][C:4]=2[F:24])[O:22][CH3:23])=[CH:15][CH:16]=1)#[N:21]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of (RS)-2-(4-bromo-2,6-difluoro-phenyl)-N-(4-cyano-benzyl)-2-methoxy-acetamide (example 69.1, 247 mg) in 1,2-dimethoxyethane (5 ml) was added tetrakis(triphenylphosphine) palladium (0) (73 mg). A solution of phenylboronic acid (118 mg) in EtOH (2.1 ml) and a solution of sodium carbonate (563 mg) in water (3 ml) were added. The mixture was stirred for 1.5 h at 85° C. The solids were filtered off and the filtrate was evaporated. The product was purified by flash chromatography (cyclohexane/EtOAc 2:1=>EtOAc) to give (RS)-N-(4-cyano-benzyl)-2-(3,5-difluoro-biphenyl-4-yl)-2-methoxy-acetamide (172 mg). Off-white solid. MS 393.1 ([M+H]+)

Workup

filtrationThe solids were filtered off
customthe filtrate was evaporated
customThe product was purified by flash chromatography (cyclohexane/EtOAc 2:1=>EtOAc)

Sources & evidence

ORD record: ord-ec93b54ad07544479477d951a0521ae3
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07129238B2

Reaction notes

Loading…