4-Vinylpyridine → HCID 470745, compound

HRID 724938Notes

Reaction equation

HRID 724938 reaction equation
Br[C:2]1[CH:21]=[N:20][C:5]2[N:6]([CH2:18][CH3:19])[C:7]3[N:16]=[C:15]([F:17])[CH:14]=[CH:13][C:8]=3[N:9]([CH3:12])[C:10](=[O:11])[C:4]=2[CH:3]=1.[CH:22]([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)=[CH2:23].CCN(C(C)C)C(C)C>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>[CH2:18]([N:6]1[C:5]2[N:20]=[CH:21][C:2]([CH2:23][CH2:22][C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)=[CH:3][C:4]=2[C:10](=[O:11])[N:9]([CH3:12])[C:8]2[CH:13]=[CH:14][C:15]([F:17])=[N:16][C:7]1=2)[CH3:19]

Participants

5

Reactant 3

HCID 75024-VinylpyridineHCID 81531DiisopropylethylamineHCID 108078258-Bromo-2-fluoro-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Product 1

HCID 470745HCID 470745, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

8-Bromo-2-fluoro-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (70 mg, 0.2 mmol) was coupled with 4-vinylpyridine in the presence of bis(triphenylphosphine)palladium(II) chloride and (i-Pr)2NEt as described in example 1h. The product was hydrogenated as described in example 3b. Purification by flash chromatography (elution with methanol-dichloromethane) and recrystallization (diethyl ether-petroleum ether) afforded 26 mg of the title compound as white crystals, m.p. 109°-111° C.

Workup

  1. customas described in example 1h
  2. customPurification
  3. washby flash chromatography (elution with methanol-dichloromethane) and recrystallization (diethyl ether-petroleum ether)

Sources & evidence

ORD record
ord-9404a165a2a0483eb7228a1d85c1289d
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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