2-Bromopropane → 2,3,4,5-Tetrahydro-5-(1-methylethyl)-1H-pyrido[4,3-b]indol-1-one

HRID 2379140Notes

Reaction equation

HRID 2379140 reaction equation
[C:1]1(=[O:14])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH2:4][CH2:3][NH:2]1.[H-].[Na+].Br[CH:18]([CH3:20])[CH3:19]>>[CH3:19][CH:18]([N:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[C:13]2[C:1](=[O:14])[NH:2][CH2:3][CH2:4][C:5]1=2)[CH3:20]

Participants

4

Reactant 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 156163232,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indol-1-one

Product 1

HCID 189577352,3,4,5-Tetrahydro-5-(1-methylethyl)-1H-pyrido[4,3-b]indol-1-oneYield 28.4%

Procedure

2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indol-1-one (931 mg) was treated with sodium hydride (73% dispersion in oil; 328 mg) and was then stirred with 2-bromopropane (615 mg) at room temperature for 72 h. Purification by FCC eluting with System A (200:8:1) gave a foam (324 mg) which was further purified by recrystallisation from ethyl acetate: hexane (1:1) to give the title compound (249 mg), t.l.c. (System A, 100:8:1) Rf 0.58.

Workup

  1. customPurification by FCC
  2. washeluting with System A (200:8:1)

Sources & evidence

ORD record
ord-dd19cbde099b45278253f26a105e75f0
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

Loading…