3-(Tributylstannyl)pyridine → 4-(3-Chloro-4-fluorophenyl)-3-pyridin-3-yl-6-[4-(3-trifluoromethylpyridin-2-yl)-piperazin-1-yl]-pyrimidine

HRID 230973

반응식

HRID 230973 반응식
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Cl:15])[CH:9]=2)[CH:5]=[C:4]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)[N:3]=1.C([Sn](CCCC)(CCCC)[C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=1)CCC>C1(C)C=CC=CC=1.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>[Cl:15][C:10]1[CH:9]=[C:8]([C:6]2[N:7]([C:37]3[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=3)[CH2:2][N:3]=[C:4]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[C:27]([C:28]([F:29])([F:31])[F:30])=[CH:26][CH:25]=[CH:24][N:23]=4)[CH2:18][CH2:17]3)[CH:5]=2)[CH:13]=[CH:12][C:11]=1[F:14]

참가 물질

5

반응물 2

HCID 34838483-(Tributylstannyl)pyridineHCID 577614902-Chloro-4-(3-chloro-4-fluoro-phenyl)-6-[4-(3-trifluoromethylpyridin-2-yl)-piperazin-1-yl]-pyrimidine

생성물 1

HCID 688262794-(3-Chloro-4-fluorophenyl)-3-pyridin-3-yl-6-[4-(3-trifluoromethylpyridin-2-yl)-piperazin-1-yl]-pyrimidine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

Heat a mixture of 2-chloro-4-(3-chloro-4-fluoro-phenyl)-6-[4-(3-trifluoromethylpyridin-2-yl)-piperazin-1-yl]-pyrimidine, (47 mg, 0.1 mmol), 3-tri-n-butylstannylpyridine (92 mg, 0.25 mmol), Pd(PPh3)4 (6 mg, 0.005 mmol), in toluene (5 mL) at 110° C. for 16 hours. Let cool to room temperature, filter off the catalyst, and add water (5 mL). Extract with EtOAc, dry (Na2SO4), and evaporate. Purify using flash chromatography (9:1 hexanes/EtOAc) to give pure 4-(3-chloro-4-fluorophenyl)-3-pyridin-3-yl-6-[4-(3-trifluoromethylpyridin-2-yl)-piperazin-1-yl]-pyrimidine as a tan solid. 1H NMR (DMSO D6): 9.75 (s, 1H). 9.21 (d, 1H), 8.97 (d, 1H), 8.62 (d, 1H), 8.58 (d, 1H), 8.40 (dd, 1H), 8.19 (d, 1H), 8.00 (d, 1H), 7.61 (d, 1H), 7.58 (s, 1H), 7.21 (dd, 1H), 4.01 (br m, 8H).

후처리

  1. temperatureHeat
  2. filtrationfilter off the catalyst
  3. additionadd water (5 mL)
  4. extractionExtract with EtOAc
  5. dry with materialdry (Na2SO4)
  6. customevaporate
  7. customPurify

출처 및 근거

ORD 기록
ord-0b673b15f0a34adb9908d9b0098080a8
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566712B2

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