1-Methyl-5-(tri-n-butylstannyl)imidazole → (1-Benzyl-1H-indazol-5-yl)-(6-(3-methyl-3H-imidazol-4-yl)-pyrido[3,4-d]pyrimidin-4-yl)-amine

HRID 2085951ノート

反応式

HRID 2085951 の反応式
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:19]4[CH:27]=[C:26](Cl)[N:25]=[CH:24][C:20]=4[N:21]=[CH:22][N:23]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:29][N:30]1[C:34]([Sn](CCCC)(CCCC)CCCC)=[CH:33][N:32]=[CH:31]1>O1CCOCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Ag]=O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:19]4[CH:27]=[C:26]([C:34]5[N:30]([CH3:29])[CH:31]=[N:32][CH:33]=5)[N:25]=[CH:24][C:20]=4[N:21]=[CH:22][N:23]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 2

HCID 109156511-Methyl-5-(tri-n-butylstannyl)imidazoleHCID 21952012(1-Benzyl-1H-indazol-5-yl)-(6-chloropyrido[3,4-d]pyrimidin-4-yl)-amine

生成物 1

HCID 22727432(1-Benzyl-1H-indazol-5-yl)-(6-(3-methyl-3H-imidazol-4-yl)-pyrido[3,4-d]pyrimidin-4-yl)-amine収率 20%

試薬・触媒・溶媒 3

HCID 92152Silver(II) oxide触媒HCID 10974057(Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1)触媒HCID 312751,4-Dioxane溶媒

実験手順

(1-Benzyl-1H-indazol-5-yl)-(6-chloro-pyrido[3,4-d]pyrimidin-4-yl)-amine (0.70 g, 1.81 mmol), 1-methyl-5-[tri(n-butyl)stannyl]imidazole (prepared according to the published method: K. Gaare et. al., Acta Chem. Scand., (1993), 47(1), p57-62) (2.2 g, 6 mmol), 1,4-bis(diphenylphosphino)-butane palladium (II) chloride (0.41 g, 0.7 mmol) and silver oxide (0.224 g, 1.8 mmol) were reacted in dry dioxane according to Procedure B. Purification by silica gel chromatography, eluting with 10%MeOH/EtOAc, gave the product as a pale brown solid (0.16 g, 0.37 mmol, 20%); δH CDCl3 10.62 (1H,s), 9.25 (1H,s), 8.75 (1H,s), 8.60 (1H,s), 8.13 (1H,s), 8.03 (1H,s), 7.20-7.78 (9H,m), 5.61 (2H,s), 3.96 (3H,s); m/z (M+1+) 433.

後処理

  1. customPurification by silica gel chromatography
  2. washeluting with 10%MeOH/EtOAc

出典と根拠

ORDレコード
ord-5f2ef40945414ca3934e7dcea0b55b46
出典データセット
uspto-grants-2004_04
特許番号
US06723726B1

反応ノート

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