3,7-Dibromo-1,5-naphthyridine → 3-Bromo-7-[2-ethoxyvinyl]-1,5-naphthyridine

HRID 11325

반응식

HRID 11325 반응식
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[N:9][CH:8]=[C:7]([Br:12])[CH:6]=2.[CH2:13]([O:15][CH:16]=[CH:17][Sn](CCCC)(CCCC)CCCC)[CH3:14]>[Cl-].C([N+](CC)(CC)CC)C.[Pd].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.CN(C)C=O>[Br:12][C:7]1[CH:8]=[N:9][C:10]2[C:5]([CH:6]=1)=[N:4][CH:3]=[C:2]([CH:14]=[CH:13][O:15][CH2:16][CH3:17])[CH:11]=2

참가 물질

7

반응물 2

HCID 12366583,7-Dibromo-1,5-naphthyridineHCID 2763294(Z)-1-Ethoxy-2-(tributylstannyl)ethene

생성물 1

HCID 670823433-Bromo-7-[2-ethoxyvinyl]-1,5-naphthyridine

시약·촉매·용매 4

HCID 5946Tetraethylammonium Chloride촉매HCID 23938Palladium촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

1,5-Naphthyridines of formula (53), wherein n is 0 or 1, and L2, L3, R4, R5, R6a and R6b are as defined in formula (I), can be prepared as described in Scheme 10. 3,7-Dibromo-[1,5]naphthyridine, prepared as described by W. W. Paudler, J. Org. Chem., 33:1384 (1968), can be treated with (2-ethoxyvinyl)tributylstannane, a halide source, such as, but not limited to, tetraethylammonium chloride, and a palladium source, such as, but not limited to, dichlorobis(triphenylphosphine)palladium (II) in a solvent, such as, but not limited to, N,N-dimethylformamide with heat (about 50° C. to about 150° C.) to provide 3-bromo-7-[2-ethoxyvinyl]-1,5-naphthyridine. 3-Bromo-7-[2-ethoxyvinyl]-1,5-naphthyridine can be treated with an acid, such as, but not limited to, 88% formic acid at about 0° C. to about 60° C. in a solvent, such as, but not limited to, 1,2-dichloroethane to provide (7-bromo-1,5-naphthyridin-3-yl)acetaldehyde. Alternatively, 3-bromo-7-[2-ethoxyvinyl]-1,5-naphthyridine in a solvent, such as, but not limited to, tetrahydrofuran can be treated with an aqueous acid, such as, but not limited to, hydrochloric acid at about 0° C. to about 60° C. to provide (7-bromo-1,5-naphthyridin-3-yl)acetaldehyde. (7-Bromo-1,5-naphthyridin-3-yl)acetaldehyde can be treated with an amine of formula (5) under reductive amination conditions, such as, but not limited to, sodium triacetoxyborohydride and an acid, such as, but not limited to, acetic acid in a solvent, such as, but not limited to, 1,2-dichloroethane at about 0° C. to about 50° C. to provide amines of formula (52). Amines of formula (52) can be processed as Schemes 1, 2, 3 and 4 to provide 1,5-naphthyridines of formula (53).

후처리

  1. customcan be prepared

출처 및 근거

ORD 기록
ord-f01f8c743b97441396e61836194bfa52
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098222B2

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