N,O-Dimethylhydroxylamine → 7-Bromo-N-methoxy-N-methyl-3-benzofurancarboxamide

HRID 2173292Notes

Reaction equation

HRID 2173292 reaction equation
[Br:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([C:11]([OH:13])=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:26][NH:27][O:28][CH3:29]>C(Cl)Cl>[Br:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([C:11]([N:27]([O:28][CH3:29])[CH3:26])=[O:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14232N,O-DimethylhydroxylamineHCID 682631,1'-CarbonyldiimidazoleHCID 656695287-bromobenzofuran-3-carboxylic acid

Product 1

HCID 772306517-Bromo-N-methoxy-N-methyl-3-benzofurancarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-bromo-1-benzofuran-3-carboxylic acid (8.9 g, 37 mmol), CDI (9.1 g, 56 mmol) and DCM (200 mL) was stirred for 4 hours at room temperature, and then MeNHOMe (5.5 g, 56 mmol) was added. The reaction mixture was stirred for 16 hours at room temperature. The reaction mixture was extracted with EtOAc (300 mL). The organic layer was washed with brine (50 mL), dried over Na2SO4. The solvent was concentrated in vacua. The residue was purified with silica gel chromatography to give 7-bromo-N-methoxy-N-methyl-1-benzofuran-3-carboxamide. 1H-NMR (400 MHz, CDCL3) δ ppm 8.33 (s, 1H), 8.21 (d, J=8.0, 1 H), 7.51 (d, J=7.6 Hz, 1H), 7.22 (t, J=8.0 Hz, 1H), 3.72 (s, 3H), 3.39 (s, 1H).

Workup

  1. stirringThe reaction mixture was stirred for 16 hours at room temperature
  2. extractionThe reaction mixture was extracted with EtOAc (300 mL)
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationThe solvent was concentrated in vacua
  6. customThe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-e5abf742a7964d4bbd9a7940a17f3c98
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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