Tributylvinyltin → 2-(6-chloro-3-vinylpyridazin-4-yl)-4-fluoro-1H-indole

HRID 595709노트

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HRID 595709 반응식
Cl[C:2]1[N:3]=[N:4][C:5]([Cl:18])=[CH:6][C:7]=1[C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[C:14]([F:17])[CH:13]=[CH:12][CH:11]=2.[CH2:19]([Sn](CCCC)(CCCC)C=C)[CH2:20]CC.[Li+].[Cl-]>CN(C=O)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>[Cl:18][C:5]1[N:4]=[N:3][C:2]([CH:19]=[CH2:20])=[C:7]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[C:14]([F:17])[CH:13]=[CH:12][CH:11]=3)[CH:6]=1

참가 물질

6

반응물 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 903336002-(3,6-dichloropyridazin-4-yl)-4-fluoro-1H-indole

생성물 1

HCID 903335012-(6-chloro-3-vinylpyridazin-4-yl)-4-fluoro-1H-indole수율 30.1%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

To a degassed solution of 2-(3,6-dichloropyridazin-4-yl)-4-fluoro-1H-indole (500 mg, 1.7 mmol), tributyl(vinyl)stannane (560 mg, 1.7 mmol) and LiCl (375 mg, 8.9 mmol) in DMF (5 mL) was added Pd(PPh3)2Cl2 (30 mg) under N2, and the mixture was stirred at 80° C. for 12 h. After the solvent was removed, the residue was purified by prep-TLC (PE:EtOAc=2:1) to give the product of 2-(6-chloro-3-vinylpyridazin-4-yl)-4-fluoro-1H-indole (140 mg, yield: 29%). 1H-NMR (CDCl3, 400 MHz) δ 8.71 (s, 1H), 7.61 (s, 1H), 7.16 (dd, J=10.8, 16.8 Hz, 2H), 7.03 (s, 1H), 6.87 (d, J=6.8 Hz, 2H), 6.68 (s, 1H), 5.79 (s, 1H). MS (M+H)+: 274/276.

후처리

  1. customAfter the solvent was removed
  2. customthe residue was purified by prep-TLC (PE:EtOAc=2:1)

출처 및 근거

ORD 기록
ord-58f237958662498393f24fb2e0c14e1c
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09243002B2

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