Acetic Acid → HCID 18327544, compound

HRID 1250411Notes

Reaction equation

[C:1]([C:3]1[CH:23]=[CH:22][C:6]([C:7]([N:9]2[CH2:21][CH2:20][C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[NH:12][C:11]=3[CH2:10]2)=[O:8])=[CH:5][CH:4]=1)#[N:2].CC(C)([O-])C.[K+].[C:30]([C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH2:35]Br)#[N:31].C(O)(=O)C>CN(C)C=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]2[CH2:21][CH2:20][C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([CH2:35][C:34]4[CH:37]=[CH:38][CH:39]=[C:32]([C:30]#[N:31])[CH:33]=4)[C:11]=3[CH2:10]2)=[O:8])=[CH:22][CH:23]=1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

150 mg (0.5 mmol) of 2-(4-cyano-benzoyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole were dissolved in 5 ml of dimethylformamide. 60 mg of potassium tert-butoxide were added and the mixture was stirred for 5 minutes, treated with 100 mg of 3-cyano-benzyl bromide and slowly heated up to 80° C. The mixture was acidified by addition of acetic acid and evaporated under reduced pressure. The residue was partitioned between methylene chloride and 10% aqueous sodium carbonate solution, dried and evaporated. Chromatography of the residue over 12 g of silica gel using 10% (v/v) of ethyl acetate in methylene chloride and crystallization from ethyl acetate/hexane yielded 132 mg of 2-(4-cyano-benzoyl)-9-(3-cyano-benzyl) -1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole with m.p. 178-180° C.

Workup

customevaporated under reduced pressure
customThe residue was partitioned between methylene chloride and 10% aqueous sodium carbonate solution
customdried
customevaporated
customChromatography of the residue over 12 g of silica gel using 10% (v/v) of ethyl acetate in methylene chloride and crystallization from ethyl acetate/hexane

Sources & evidence

ORD record: ord-b978fdd8b7764c0496dc6cfd741fff1a
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06337344B1

Reaction notes

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