Dimethylformamide → N-[5-(2-Cyano-pyridin-4-yl)-4-methyl-thiazol-2-yl]-2,6-difluoro-benzamide

HRID 1255117ノート

反応式

HRID 1255117 の反応式
Br[C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([NH:13][C:14](=[O:23])[C:15]3[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=3[F:22])=[N:10][C:9]=2[CH3:24])[CH:5]=[CH:4][N:3]=1.[CH3:25][N:26](C=O)C>[C-]#N.[C-]#N.[Zn+2].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>[C:25]([C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([NH:13][C:14](=[O:23])[C:15]3[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=3[F:22])=[N:10][C:9]=2[CH3:24])[CH:5]=[CH:4][N:3]=1)#[N:26]

参加物

5

反応物 2

HCID 6228DimethylformamideHCID 24765026N-[5-(2-Bromo-pyridin-4-yl)-4-methyl-thiazol-2-yl]-2,6-difluoro-benzamide

生成物 1

HCID 59004536N-[5-(2-Cyano-pyridin-4-yl)-4-methyl-thiazol-2-yl]-2,6-difluoro-benzamide

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
110 °C

実験手順

A solution of N-[5-(2-Bromo-pyridin-4-yl)-4-methyl-thiazol-2-yl]-2,6-difluoro-benzamide (100 mg, 0.24 mmol), Zn(CN)2 (43.0 mg, 0.36 mmol), and Pd(PPh3)4 (20.0 mg, 0.02 mmol) in DMF (4.0 mL) was degassed by purging with a stream of nitrogen for 10 minutes. The mixture was heated to 110° C. overnight, cooled to room temperature, diluted with CH2Cl2, washed with water, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified on silica gel to give the title compound (45 mg).

後処理

  1. customby purging with a stream of nitrogen for 10 minutes
  2. temperaturecooled to room temperature
  3. additiondiluted with CH2Cl2
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified on silica gel

出典と根拠

ORDレコード
ord-4cff4c7e3be84091b0f7da8dda9ff6e4
出典データセット
uspto-grants-2013_06
特許番号
US08455658B2

反応ノート

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