Dimethylamine → 5-bromo-N,N-dimethyl-2,3-dihydro-1-benzofuran-2-carboxamide

HRID 1778647Notes

Reaction equation

HRID 1778647 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([C:10](O)=[O:11])[CH2:7][C:6]=2[CH:13]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)[N:32]([CH3:34])[CH3:33])C2C=CC=CC=2N=N1.CNC.O1CCCC1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([C:10]([N:32]([CH3:34])[CH3:33])=[O:11])[CH2:7][C:6]=2[CH:13]=1

Participants

5

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 186242435-Bromo-2,3-dihydro-1-benzofuran-2-carboxylic acid

Product 1

HCID 867227985-bromo-N,N-dimethyl-2,3-dihydro-1-benzofuran-2-carboxamideYield 87%

Procedure

A mixture of 5-bromo-2,3-dihydro-1-benzofuran-2-carboxylic acid (0.243 g, 1.00 mmol) (ParkWay, Cat. No. YB-162), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.464 g, 1.05 mmol) and 2.0 M dimethylamine in tetrahydrofuran (THF) (2.00 mL, 4.00 mmol) was stirred at r.t. for 2 h. The volatiles were removed under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (gradient: 0-50%) to afford the desired product (0.235 g, 87%). LCMS (M+H)+=270.0/272.0.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (gradient: 0-50%)

Sources & evidence

ORD record
ord-9aae343104a34c03ae6c5224a42417c0
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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