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

HRID 506198노트

반응식

HRID 506198 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-cd84a79ac4314d75a7063b714e672672
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781591B2

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