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4-Bromoanisole → 1-(4-{4-[(4-Methoxyphenyl)ethynyl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

HRID 549969
ノート
印刷プレビュー

反応式

HRID 549969 の反応式
C(N(CC)CC)C.[CH3:8][C:9]1[N:13]([CH2:14][C:15]([N:17]2[CH2:22][CH2:21][CH:20]([C:23]3[S:24][CH:25]=[C:26]([C:28]#[C:29][Si](C)(C)C)[N:27]=3)[CH2:19][CH2:18]2)=[O:16])[N:12]=[C:11]([C:34]([F:37])([F:36])[F:35])[CH:10]=1.Br[C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:46][O:45][C:42]1[CH:43]=[CH:44][C:39]([C:29]#[C:28][C:26]2[N:27]=[C:23]([CH:20]3[CH2:21][CH2:22][N:17]([C:15](=[O:16])[CH2:14][N:13]4[C:9]([CH3:8])=[CH:10][C:11]([C:34]([F:36])([F:35])[F:37])=[N:12]4)[CH2:18][CH2:19]3)[S:24][CH:25]=2)=[CH:40][CH:41]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 77304-BromoanisoleHCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 671564122-[5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(trimethylsilyl)ethynyl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone

生成物 1

HCID 671568341-(4-{4-[(4-Methoxyphenyl)ethynyl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

Tetrakis(triphenylphosphine)palladium(0) (25 mg), copper(I) iodide (8 mg) and triethylamine (53 mg) are added to a solution of 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(trimethylsilyl)ethynyl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone (I-98, 200 mg) and 1-bromo-4-methoxybenzene (91 mg) in degassed N,N-dimethylformamide (2 ml). After warming to 85° C., tetra-n-butylammonium fluoride (1M in THF, 0.48 ml) is added dropwise. The reaction mixture is then diluted with water and extracted with ethyl acetate. The organic extracts are dried over sodium sulphate and concentrated under reduced pressure. After chromatographic purification, this gives 1-(4-{4-[(4-methoxyphenyl)ethynyl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (84 mg).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts are dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customAfter chromatographic purification

出典と根拠

ORDレコード
ord-57afe89b33f24e91a8be5564e352790f
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07943774B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート