Triethylamine → HCID 66789608, compound

HRID 1660848Notes

Reaction equation

HRID 1660848 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([O:6][CH2:7][CH2:8][N:9]2[S:12]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])(=[O:14])=[O:13])=[N:4][CH:3]=1.C(N(CC)CC)C.[C:31]([O:34][CH2:35][CH3:36])(=[O:33])C>C(O)C>[CH2:35]([O:34][C:31]([C:2]1[CH:11]=[C:10]2[C:5]([O:6][CH2:7][CH2:8][N:9]2[S:12]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[O:22][CH3:23])(=[O:14])=[O:13])=[N:4][CH:3]=1)=[O:33])[CH3:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66792590HCID 66792590, compound

Product 1

HCID 66789608HCID 66789608, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7-bromo-1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-4-oxa-1,5-diaza-naphthalene (200 mg, 0.476 mmol), triethylamine (120 mg, 1.19 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium dichloromethane complex (19 mg, 29 μmol) in ethanol (2 mL) and ethyl acetate (2 mL) was heated at 110° C. under a carbon monoxide atmosphere (70 bar) for 20 h. The reaction mixture was evaporated and the residue chromatographed (SiO2, toluene-acetonitrile gradient) to produce 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-4-oxa-1,5-diaza-naphthalene-7-carboxylic acid ethyl ester (132 mg, 67%). Off-white solid, MS (ISP)=413.2 (M+H)+.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue chromatographed (SiO2, toluene-acetonitrile gradient)

Sources & evidence

ORD record
ord-7b6e0b89fdd345178a0af049b5bb3044
Source dataset
uspto-grants-2011_10
Patent number
US08030308B2

Reaction notes

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