Water → tert-Butyl 7-bromo-3,5-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

HRID 2365413Notes

Reaction equation

HRID 2365413 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:12]([CH3:22])[CH2:11][C:7]=3[NH:8][C:9]=2[CH:10]=1.[H-].[Na+].[CH3:25]I.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:12]([CH3:22])[CH2:11][C:7]=3[N:8]([CH3:25])[C:9]=2[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67986826tert-Butyl 7-bromo-3-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Product 1

HCID 67986822tert-Butyl 7-bromo-3,5-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylateYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl 7-bromo-3-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (enantiomer A) (1.00 g, 2.73 mmol) was dissolved in DMF (10 mL), and NaH (60% disp, 131 mg, 3.28 mmol) was added. After stirring for 30 minutes, MeI (386 mg, 0.170 ml, 3.28 mmol) was added, and the reaction continued for 1 h. The mixture was poured into water (250 ml), and the solid was filtered off to provide the title compound (180 mg, 17%) as a yellow solid: ESI MS m/z 379 [M+H]+.

Workup

  1. waitthe reaction continued for 1 h
  2. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-1c629c3da15b4ba0b91e42a7d2c12f69
Source dataset
uspto-grants-2014_04
Patent number
US08697700B2

Reaction notes

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