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

HRID 591683

반응식

HRID 591683 반응식
[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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-9ca0f7c273b54587bb502bf8a4bb6f49
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238640B2

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