Benzyl Bromide → 2,3,4,5-Tetrahydro-5-(phenylmethyl)-1H-pyrido[4,3-b]indol-1-one

HRID 2379141Notes

Reaction equation

HRID 2379141 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+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:18]1([CH2:17][N:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]3[C:1](=[O:14])[NH:2][CH2:3][CH2:4][C:5]2=3)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 156163232,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indol-1-one

Product 1

HCID 156163262,3,4,5-Tetrahydro-5-(phenylmethyl)-1H-pyrido[4,3-b]indol-1-oneYield 41.9%

Procedure

2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indol-1-one (559 mg) was treated with sodium hydride (73% dispersion in oil; 197 mg) and was then stirred with benzyl bromide (513 mg) at room temperature for 30 min. Purification by FCC eluting with dichloromethan: ethanol (80:1) gave the title compound (347 mg), m.p. 209°-212°.

Workup

  1. customPurification by FCC
  2. washeluting with dichloromethan: ethanol (80:1)

Sources & evidence

ORD record
ord-7c6403773c704754961575faf751256c
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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