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

HRID 591683

Reaction equation

HRID 591683 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-9ca0f7c273b54587bb502bf8a4bb6f49
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Linked notes

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