Sodium hydride → HCID 66606378, compound

HRID 661958Notes

Reaction equation

HRID 661958 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]([C:15]([NH2:17])=[O:16])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH:7]([CH2:18][NH:19][C:20](=[O:25])[CH2:21][CH2:22][CH2:23]Br)[CH2:8][C:9]=1[NH:10]2.[H-].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[CH:14]=[CH:13][C:12]([C:15]([NH2:17])=[O:16])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH:7]([CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:25])[CH2:8][C:9]=1[NH:10]2

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 66606703HCID 66606703, compound

Product 1

HCID 66606378HCID 66606378, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Step 5 A solution of 5-bromo-2-((4-bromobutanamido)methyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (80 mg, 0.170 mmol) in DMF (1 mL) was treated with NaH (60% in mineral oil, pre-washed with hexane, 34 mg, 0.849 mmol). The mixture was stirred at rt for 30 min, the was diluted with water and extracted three times with DCM. The combined organic phases were dried and concentrated, and the residue was purified by column chromatography (eluting with 5% aqueous ammonium hydroxide-methanol-DCM) to provide 5-bromo-2-((2-oxopyrrolidin-1-yl)methyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide as a light yellow solid, used without further purification (40 mg, 60%). Mass spectrum m/z 390, 392 (M+H)+.

Workup

  1. extractionextracted three times with DCM
  2. customThe combined organic phases were dried
  3. concentrationconcentrated
  4. customthe residue was purified by column chromatography (eluting with 5% aqueous ammonium hydroxide-methanol-DCM)

Sources & evidence

ORD record
ord-14a1039009394ae8b1e404c0d0265b11
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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