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

HRID 595709ノート

反応式

HRID 595709 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-58f237958662498393f24fb2e0c14e1c
出典データセット
uspto-grants-2016_01
特許番号
US09243002B2

反応ノート

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