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

HRID 2245543ノート

反応式

HRID 2245543 の反応式
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]

参加物

8

反応物 6

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

生成物 1

HCID 102362866-Bromo-N-methyl-2-oxoindoline-5-carboxamide収率 48.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-73520ba9d3f54d63800a625675644c8a
出典データセット
uspto-grants-2010_03
特許番号
US07683067B2

反応ノート

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