4-Methylmorpholine → 5-Bromo-2-(pyrrolidine-1-carbonyl)-1H-indole

HRID 591683

反応式

HRID 591683 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.Cl.C(N=C=N[CH2:20][CH2:21][CH2:22][N:23]([CH3:25])C)C.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.N1CCCC1>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([N:23]1[CH2:22][CH2:21][CH2:20][CH2:25]1)=[O:13])=[CH:5]2

参加物

7

反応物 5

HCID 79724-MethylmorpholineHCID 31268PyrrolidineHCID 2521375-Bromo-1H-indole-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 471546575-Bromo-2-(pyrrolidine-1-carbonyl)-1H-indole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of 5-bromo-1H-indole-2-carboxylic acid (1.0 g, 4.2 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDCl) (1.1 g, 5.9 mmol), 1-hydroxybenzotriazole hydrate (HOBt) (0.62 g, 4.6 mmol) in THF (20 mL) was added 4-methylmorpholine (NMM) (0.65 mL, 5.9 mmol). After 10 minutes, pyrrolidine (0.73 mL, 8.8 mmol) was added. The mixture was stirred at room temperature under nitrogen for 17 hours. The solvent was removed under reduced pressure. Water was added, stirred for 0.5 hours. The solid was filtered, washed with water, and dried in air to afford (5-bromo-1H-indol-2-yl)-pyrrolidin-1-yl-methanone as a pale yellow solid. Yield: 1.2 g (95%).

後処理

  1. customThe solvent was removed under reduced pressure
  2. additionWater was added
  3. stirringstirred for 0.5 hours
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customdried in air

出典と根拠

ORDレコード
ord-9ca0f7c273b54587bb502bf8a4bb6f49
出典データセット
uspto-grants-2016_01
特許番号
US09238640B2

関連ノート

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