Water → HCID 58101298, compound

HRID 237321Notes

Reaction equation

HRID 237321 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH:14]3[C:26]4[NH:25][C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[C:18]=4[CH2:17][CH2:16][N:15]3[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.Br[CH2:35][C:36]#[N:37].O>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH:14]3[C:26]4[N:25]([CH2:35][C:36]#[N:37])[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[C:18]=4[CH2:17][CH2:16][N:15]3[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 58101286HCID 58101286, compound

Product 1

HCID 58101298HCID 58101298, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

60% Sodium hydride suspension in mineral oil (0.412 g, 10.3 mmol) in dry dimethylformamide (25 mL) was stirred at room temperature under an atmosphere of nitrogen. tert-Butyl 1-[1-(4-chlorophenyl)cyclobutyl]-1,3,4,9-tetrahydro-2H-b-carboline-2-carboxylate (3.0 g, 6.87 mmol) was added in small portions. After 30 min stirring at room temperature 2-bromoacetonitrile (1.235 g, 10.3 mmol) in dimethylformamide (5 mL) was added dropwise. The reaction mixture was stirred at room temperature for two days. Water was added (1 mL). The reaction mixture was concentrated in vacuo, dichloromethane (100 mL) was added and the organic solution successively washed with water (50 mL), saturated NaHCO3 solution (30 mL) and water (30 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography (silica, dichloromethane). Yield: 2.7 g (83%).

Workup

  1. additionwas added dropwise
  2. concentrationThe reaction mixture was concentrated in vacuo, dichloromethane (100 mL)
  3. additionwas added
  4. washthe organic solution successively washed with water (50 mL), saturated NaHCO3 solution (30 mL) and water (30 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (silica, dichloromethane)

Sources & evidence

ORD record
ord-9a794e79823f45a59022027d2b83d555
Source dataset
uspto-grants-2014_02
Patent number
US08642587B2

Reaction notes

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