Dimethylacetamide → HCID 66982705, compound

HRID 516250Notes

Reaction equation

Br[C:2]1[C:3]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16][C:4]=2[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH2:13][O:14][CH3:15])[CH2:9][CH2:8][CH2:7]2.[CH3:28][N:29](C)C(=O)C>[C-]#N.[Zn+2].[C-]#N.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.[Zn]>[C:28]([C:2]1[C:3]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16][C:4]=2[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH2:13][O:14][CH3:15])[CH2:9][CH2:8][CH2:7]2)#[N:29]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 200 mg of t-butyl 11-bromo-1-(2-methoxyethyl)-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate, 34 mg of zinc cyanide, 13 mg of bis(tri-t-butylphosphine)palladium, and 10 mg of zinc powder in 4 ml of N,N-dimethylacetamide was substituted with argon and then stirred at 100° C. for 15 hours. The reaction mixture was purified by silica gel chromatography (elution solvent: HEX-EtOAc) to obtain 132 mg of t-butyl 11-cyano-1-(2-methoxyethyl)-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate as a colorless viscous substance.

Workup

customThe reaction mixture was purified by silica gel chromatography (elution solvent: HEX-EtOAc)

Sources & evidence

ORD record: ord-5734e9b8d7044230a64a6d590d11eb62
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108977B2

Reaction notes

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