3-Fluorostyrene → 2-Chloro-5,11-dihydro-11-ethyl-8-[2-(3-fluorophenyl)ethen-1-yl]-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 724929Notes

Reaction equation

HRID 724929 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:21])[C:7](=[O:20])[C:8]3[CH:18]=[C:17](I)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.[F:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=[CH2:27]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:21])[C:7](=[O:20])[C:8]3[CH:18]=[C:17]([CH:27]=[CH:26][C:25]4[CH:28]=[CH:29][CH:30]=[C:23]([F:22])[CH:24]=4)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1

Participants

5

Reactant 2

HCID 676913-FluorostyreneHCID 107643002-Chloro-5,11-dihydro-11-ethyl-8-iodo-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Product 1

HCID 867518392-Chloro-5,11-dihydro-11-ethyl-8-[2-(3-fluorophenyl)ethen-1-yl]-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

By a procedure analogous to that described in Example 1h, 2-chloro-5,11-dihydro-11-ethyl-8-iodo-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one was coupled with 3-fluorostyrene in the presence of bis(triphenylphosphine)palladium(II) chloride and triethylamine. The product was hydrogenated by a procedure analogous to that described in Example 15 to give 16 mg of the title compound, m.p. 130°-131° C. (ethyl acetate/hexanes).

Sources & evidence

ORD record
ord-0582bdec13f243c8b393877d727f7753
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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