Methylamine → 1-Acetyl-5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonic acid methylamide

HRID 1475323ノート

反応式

HRID 1475323 の反応式
[CH3:1][NH2:2].[C:3]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([Br:19])=[C:12]([S:15](Cl)(=[O:17])=[O:16])[CH:13]=2)[C:8]([CH3:21])([CH3:20])[CH2:7]1)(=[O:5])[CH3:4]>C1COCC1>[CH3:1][NH:2][S:15]([C:12]1[CH:13]=[C:14]2[C:9]([C:8]([CH3:21])([CH3:20])[CH2:7][N:6]2[C:3](=[O:5])[CH3:4])=[CH:10][C:11]=1[Br:19])(=[O:17])=[O:16]

参加物

4

反応物 2

HCID 6329MethylamineHCID 867239431-Acetyl-5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonyl chloride

生成物 1

HCID 709804931-Acetyl-5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonic acid methylamide収率 91.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Methylamine (2 M solution in THF, 2.4 mL, 4.9 mmol) was added to a solution of 1-acetyl-5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole-6-sulfonyl chloride (300 mg, 0.82 mmol) in THF (10 mL). The solution was stirred at room temperature for 30 minutes then the solvent was removed in vacuo and the residue partitioned between water and EtOAc. The organic phase was dried (MgSO4), filtered and concentrated to give the title compound (271 mg) as a yellow solid. 1H NMR (CDCl3): 8.93 (1H, s), 7.44 (1H, s), 5.07 (1H, s), 3.88 (2H, s), 2.68 (3H, d), 2.25 (3H, s), 1.48-1.22 (6H, s).

後処理

  1. customthe solvent was removed in vacuo
  2. customthe residue partitioned between water and EtOAc
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-0c2394c4753c41aba27788f136bc4d90
出典データセット
uspto-grants-2015_04
特許番号
US09018214B2

反応ノート

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