Water → HCID 86669348, compound

HRID 924951Notes

Reaction equation

HRID 924951 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O>[C:2]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 62735316HCID 62735316, compound

Product 1

HCID 86669348HCID 86669348, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of 2-(3-bromophenyl)-N-methoxy-N-methylacetamide (2.0 g, 7.7 mmol), phenylboronic acid (1.42 g, 11.6 mmol), 1-1′-bis(diphenylphosphino)derrocene palladium dichloride (500 mg, 0.77 mmol), and saturated aqueous sodium carbonate solution (1 mL) in N,N-dimethylformamide (20 mL) was heated at 80° C. under N2 overnight. The mixture was poured into water, extracted with EA, dried over Na2SO4, concentrated in vacuo, and purified by column chromatography (PE:EtOAc=30:1-10:1) to afford 2-(biphenyl-3-yl)-N-methoxy-N-methylacetamide (1.8 g, yield 94.7%).

Workup

  1. extractionextracted with EA
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by column chromatography (PE:EtOAc=30:1-10:1)

Sources & evidence

ORD record
ord-c7e2d5c2629d40e4ab2b21c4b9569876
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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