Methylamine → 6-Bromo-N-methyl-2-oxoindoline-5-carboxamide

HRID 2245543노트

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HRID 2245543 반응식
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]

참가 물질

8

반응물 6

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

생성물 1

HCID 102362866-Bromo-N-methyl-2-oxoindoline-5-carboxamide수율 48.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-73520ba9d3f54d63800a625675644c8a
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07683067B2

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