Methylamine → 6-Bromo-2,3-dihydro-N-methyl-2-oxo-1H-indole-5-carboxamide

HRID 2245543Notes

Reaction equation

HRID 2245543 reaction equation
CN.[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][C:9](=[O:13])[NH:10]2)=[CH:6][C:5]=1[C:14]([OH:16])=O.F[B-](F)(F)F.[N:22]1(OC(N(C)C)=[N+](C)C)[C:26]2C=CC=CC=2N=N1.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][C:9](=[O:13])[NH:10]2)=[CH:6][C:5]=1[C:14]([NH:22][CH3:26])=[O:16]

Participants

8

Reactant 6

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27960291-Hydroxybenzotriazole hydrateHCID 10192821HCID 10192821, compound

Product 1

HCID 102362866-Bromo-2,3-dihydro-N-methyl-2-oxo-1H-indole-5-carboxamideYield 48.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methylamine (0.75 mL, 2.0 M in tetrahydrofuran) was added to a stirred solution of 6-bromo-2-oxoindoline-5-carboxylic acid (0.246 g, 0.96 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.369 g, 1.15 mmol), 1-hydroxybenzotriazole hydrate (0.176 g, 1.15 mmol), and diisopropylethylamine (0.55 mL, 3.16 mmol) in dry N,N-dimethylformamide (4 mL) under an atmosphere of nitrogen. The resulting mixture was stirred at room temperature for 1.5 h. An aqueous solution of sodium bicarbonate was added and the solvent was evaporated. The resulting residue was purified on a silica gel column using dichloromethane/methanol, (9:1), as the eluent to give 0.125 g (48% yield) of the title compound: 1H NMR (CD3OD, 400 MHz) δ 7.27 (s, 1H), 7.11 (s, 1H), 3.20 (m, 2H), 3.09 (s, 3H); MS (ES) m/z 269 and 271 (M++1).

Workup

  1. customthe solvent was evaporated
  2. customThe resulting residue was purified on a silica gel column

Sources & evidence

ORD record
ord-73520ba9d3f54d63800a625675644c8a
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

Loading…