4-Chloroaniline → N-(4-chlorophenyl)-6-(6,7-dimethoxyquinolin-4-yloxy)benzofuran-3-carboxamide

HRID 1865217Notes

Reaction equation

HRID 1865217 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:27]=[CH:26][C:19]2[C:20]([C:23](O)=[O:24])=[CH:21][O:22][C:18]=2[CH:17]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[Cl:50][C:51]1[CH:57]=[CH:56][C:54]([NH2:55])=[CH:53][CH:52]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Cl:50][C:51]1[CH:57]=[CH:56][C:54]([NH:55][C:23]([C:20]2[C:19]3[CH:26]=[CH:27][C:16]([O:15][C:6]4[C:5]5[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=5)[N:9]=[CH:8][CH:7]=4)=[CH:17][C:18]=3[O:22][CH:21]=2)=[O:24])=[CH:53][CH:52]=1

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 690186826-(6,7-Dimethoxyquinolin-4-yloxy)benzofuran-3-carboxylic acid

Product 1

HCID 57975990N-(4-chlorophenyl)-6-(6,7-dimethoxyquinolin-4-yloxy)benzofuran-3-carboxamideYield 12.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(6,7-Dimethoxyquinolin-4-yloxy)benzofuran-3-carboxylic acid (31 mg, 0.085 mmol) and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (41 mg, 0.127 mmol) were added to a reaction tube then dissolved in DMF (0.6 mL). 4-chloroaniline (13 mg, 0.102 mmol) was added to the reaction mixture, followed by N,N-diisopropylethylamine (22 mg, 0.17 mmol) and stirring was continued for 2 days. The mixture was concentrated in vacuo. The remaining orange oil was purified by silica gel chromatography (1% to 2% methanol in dichloromethane) to afford N-(4-chlorophenyl)-6-(6,7-dimethoxyquinolin-4-yloxy)benzofuran-3-carboxamide as a yellow solid (5 mg). MS (ESI, pos. ion) m/z: 475.1 (M+1). Mass calc'd for C26H19ClN2O5: 474.89.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe remaining orange oil was purified by silica gel chromatography (1% to 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-601e30b1dbef4c9f93f52ca5b518f8be
Source dataset
uspto-grants-2009_12
Patent number
US07626030B2

Reaction notes

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