Ammonia → HCID 18183106, compound

HRID 430668Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]2[CH2:10][C:9]3[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:8]=3[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:6][N:5]2[C:23]=1[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1.[CH2:30]([O:32]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:31].Cl.N>C1(C)C=CC=CC=1.C(OCC)(=O)C.CN(C)C=O>[C:30]([C:2]1[N:3]=[C:4]2[CH2:10][C:9]3[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:8]=3[C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:6][N:5]2[C:23]=1[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)(=[O:32])[CH3:31]

Participants

Conditions

Temperature: 120 °C

Procedure

82 mg of 2-bromo-3-(3-pyridyl)-8-methoxy-6-phenyl-11H-imidazo[1,2-c][2,3]benzodiazepine is mixed in 3 ml of toluene and 0.5 ml of dimethylformamide with 650 mg of (1-ethoxyvinyl)tributylstannane and 10 mg of palladium(O)tetrakistriphenylphosphine, and it is heated for 4 hours to a bath temperature of 120° C. Then, (1-ethoxyvinyl)tributylstannane and 10 mg of palladium(O)tetrakistriphenylphosphine are added again, and it is heated for 10 hours to a bath temperature of 120° C. After cooling, it is mixed with 2 ml of 1N hydrochloric acid, stirred for 10 minutes, made alkaline with ammonia and shaken out with ethyl acetate. The ethyl acetate phase is washed with water and saturated common salt solution, dried, filtered and concentrated by evaporation. After chromatography of the residue on silica gel with ethyl acetate as an eluant, 20 mg of 2-acetyl-3-(3-pyridyl)-8-methoxy-6-phenyl-11H-imidazo[1,2-c][2,3]benzodiazepine is obtained.

Workup

temperatureAfter cooling
washThe ethyl acetate phase is washed with water and saturated common salt solution
customdried
filtrationfiltered
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-bafc346ea4cb4294be1f17bd71066cda
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06323197B1

Reaction notes

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