Triethylamine → 1-(5-chloro-2-methoxybenzenesulfonyl)-1,4-dihydro-2H-benzo[d][1,3]oxazine-7-carboxylic acid methyl ester

HRID 641340Notes

Reaction equation

HRID 641340 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH2:10][O:9][CH2:8][N:7]([S:11]([C:14]3[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=3[O:21][CH3:22])(=[O:13])=[O:12])[C:6]=2[CH:23]=1.C(N(CC)CC)C.[C:31]([O:34][CH2:35]C)(=[O:33])C>CO>[CH3:35][O:34][C:31]([C:2]1[CH:3]=[CH:4][C:5]2[CH2:10][O:9][CH2:8][N:7]([S:11]([C:14]3[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=3[O:21][CH3:22])(=[O:13])=[O:12])[C:6]=2[CH:23]=1)=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 667890607-bromo-1-(5-chloro-2-methoxy-benzenesulfonyl)-1,4-dihydro-2H-benzo[d][1,3]oxazine

Product 1

HCID 667898161-(5-chloro-2-methoxybenzenesulfonyl)-1,4-dihydro-2H-benzo[d][1,3]oxazine-7-carboxylic acid methyl esterYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7-bromo-1-(5-chloro-2-methoxy-benzenesulfonyl)-1,4-dihydro-2H-benzo[d][1,3]oxazine (2.00 g, 4.78 mmol), triethylamine (1.21 g, 11.9 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium dichloromethane complex (200 mg, 0.239 mmol) in methanol (30 mL) and ethyl acetate (30 mL) was heated at 130° C. under a carbon monoxide atmosphere (100 bar) for 3 h. The reaction mixture was evaporated and the residue chromatographed (SiO2, heptane-ethyl acetate gradient) to produce 1-(5-chloro-2-methoxy-benzenesulfonyl)-1,4-dihydro-2H-benzo[d][1,3]oxazine-7-carboxylic acid methyl ester (825 mg, 43%). Orange solid, MS (ISP)=398.1 (M+H)+.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue chromatographed (SiO2, heptane-ethyl acetate gradient)

Sources & evidence

ORD record
ord-cb81821a2bd040fb90334ee4344f0745
Source dataset
uspto-grants-2010_04
Patent number
US07696200B2

Reaction notes

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