(4aS,9bR)-8-bromo-6-cyano-5-methyl-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl ester → (4aS,9bR)-5-methyl-8-phenethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole-6-carbonitrile

HRID 2215936Notes

Reaction equation

HRID 2215936 reaction equation
C(OC([N:8]1[CH2:24][CH2:23][C@@H:11]2[N:12]([CH3:22])[C:13]3[C:14]([C:20]#[N:21])=[CH:15][C:16](Br)=[CH:17][C:18]=3[C@@H:10]2[CH2:9]1)=O)(C)(C)C.[Br-].[CH2:26]([Zn+])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:22][N:12]1[C:13]2[C:18](=[CH:17][C:16]([CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:15][C:14]=2[C:20]#[N:21])[C@@H:10]2[CH2:9][NH:8][CH2:24][CH2:23][C@H:11]12

Participants

4

Reactant 2

HCID 58700289(4aS,9bR)-8-bromo-6-cyano-5-methyl-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl esterHCID 178419778HCID 178419778, compound

Product 1

HCID 58700285(4aS,9bR)-5-methyl-8-phenethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Following the general procedure for Examples 127–146, the title compound was prepared (8 mg, 25%) as a light yellow oil using (4aS,9bR)-8-bromo-6-cyano-5-methyl-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indole-2-carboxylic acid tert-butyl ester (Example 158, 40 mg, 0.10 mmol), phenethylzinc bromide (0.5 M in THF, 2.5 mole equivalent) and Pd(PPh3)4 (0.06 mole equivalent).: MS (ESI): 318 (base, M+H).

Sources & evidence

ORD record
ord-16053d1f77884d2d96e3cf4bec2a45ed
Source dataset
uspto-grants-2006_09
Patent number
US07109339B2

Reaction notes

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