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

HRID 1255117노트

반응식

HRID 1255117 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매

반응 조건

온도
110 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4cff4c7e3be84091b0f7da8dda9ff6e4
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455658B2

반응 노트

불러오는 중…