2-Bromo-5-chlorophenylboronic acid → tert-Butyl [4-(2-bromo-5-chlorophenyl)-2-oxopyridin-1(2H)-yl]acetate

HRID 56681Notes

Reaction equation

HRID 56681 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:4](=[O:16])[CH:3]=1.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1B(O)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>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[C:2]1[CH:7]=[CH:6][N:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:4](=[O:16])[CH:3]=1

Participants

4

Reactant 2

HCID 445581362-Bromo-5-chlorophenylboronic acidHCID 117622649tert-Butyl (4-bromo-2-oxopyridin-1(2H)-yl)acetate

Product 1

HCID 117622756tert-Butyl [4-(2-bromo-5-chlorophenyl)-2-oxopyridin-1(2H)-yl]acetate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

3.8 g (12 mmol) of tert-butyl (4-bromo-2-oxopyridin-1(2H)-yl)acetate and 3.4 g (14.4 mmol) of 2-bromo-5-chlorophenylboronic acid in the presence of tetrakis(triphenylphosphine)palladium(0) were reacted according to General Method 2A. Yield: 3.9 g (purity 94%, 76% of theory)

Sources & evidence

ORD record
ord-af82689336fe49ba992dc6ef4b1c66a6
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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