Triethylamine → 5-(2-formyl-1-methyl-1H-imidazol-5-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile

HRID 506198ノート

反応式

HRID 506198 の反応式
I[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:9]=1[NH:10][C:11]1[C:12]([CH3:20])=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)[C:7]#[N:8].[CH3:21][N:22]1[C:26]([Sn](CCCC)(CCCC)CCCC)=[CH:25][N:24]=[C:23]1[CH:40]=[O:41].C(N(CC)CC)C>O1CCOCC1.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>[CH:40]([C:23]1[N:22]([CH3:21])[C:26]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([C:9]=2[NH:10][C:11]2[C:12]([CH3:20])=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[CH:14]3)[C:7]#[N:8])=[CH:25][N:24]=1)=[O:41]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 222566721-methyl-5-(tributylstannyl)-1H-imidazole-2-carbaldehydeHCID 684438315-iodo-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile

生成物 1

HCID 866168365-(2-formyl-1-methyl-1H-imidazol-5-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile収率 43%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 5-iodo-4[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile (250 mg, 0.67 mmol), 1-methyl-5-(tributylstannyl)-1H-imidazole-2-carbaldehyde (see e.g., U.S. Pat. No. 6,521,618) (401 mg, 1.0 mmol), dichlorobis(triphenylphosphine)palladium(II) (24 mg, 0.034 mmol), and triethylamine (74.9 mg, 0.74 mmol) in dioxane (6 mL) was heated at the reflux temperature for 22 h, cooled to room temperature, and concentrated in vacuo. The residue was suspended in CH2Cl2 and filtered and the solid was washed with CH2Cl2. The combined filtrate and washings were concentrated in vacuo and the residue was purified by column chromatography (ethyl acetate/CH2Cl2, 20% to 90%; MeOH/ethyl acetate, 5%) to provide 103 mg (43%) of 5-(2-formyl-1-methyl-1H-imidazol-5-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile 537 as a dark yellow solid. MS: 355.2 (M+H); melting range: 200-202° C.; and HRMS: 357.1458.

後処理

  1. concentrationconcentrated in vacuo
  2. filtrationfiltered
  3. washthe solid was washed with CH2Cl2
  4. concentrationThe combined filtrate and washings were concentrated in vacuo
  5. customthe residue was purified by column chromatography (ethyl acetate/CH2Cl2, 20% to 90%; MeOH/ethyl acetate, 5%)

出典と根拠

ORDレコード
ord-cd84a79ac4314d75a7063b714e672672
出典データセット
uspto-grants-2010_08
特許番号
US07781591B2

反応ノート

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