Potassium Carbonate → Benzyl 3-(5-cyano-2-(methylthio)pyrimidin-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-ylcarbamate

HRID 40864노트

반응식

HRID 40864 반응식
CC1(C)C(C)(C)OB([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:16]=3)[N:11]([S:29]([C:32]3[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=3)(=[O:31])=[O:30])[CH:10]=2)O1.Cl[C:41]1[C:46]([C:47]#[N:48])=[CH:45][N:44]=[C:43]([S:49][CH3:50])[N:42]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:47]([C:46]1[C:41]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:16]=3)[N:11]([S:29]([C:32]3[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=3)(=[O:30])=[O:31])[CH:10]=2)=[N:42][C:43]([S:49][CH3:50])=[N:44][CH:45]=1)#[N:48]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileHCID 59414528Benzyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-ylcarbamate

생성물 1

HCID 68668331Benzyl 3-(5-cyano-2-(methylthio)pyrimidin-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-ylcarbamate수율 42.2%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 21863594Toluene ethanol용매

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온도
100 °C

실험 절차

Benzyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-ylcarbamate (0.50 g, 0.91 mmol) in toluene/ethanol (7.5 mL:2.0 mL) was treated with 4-chloro-2-(methylthio)pyrimidine-5-carbonitrile (0.186 g, 1.00 mmol, 1.1 Eq) and 2M aqueous potassium carbonate (1.37 mL, 2.74 mmol, 3.0 Eq), degassed and stirred under nitrogen for 20 minutes. Pd(dppf)2Cl2 (0.075 g, 0.1 Eq) was added and the mixture allowed to heat at 100° C. for 1.5 hours. The reaction was partitioned between EtOAc and saturated aqueous sodium carbonate and the organic layer separated, dried over magnesium sulphate and evaporated to dryness. The mixture was purified by column chromatography eluting with 10% EtOAc/Petroleum ether to yield a white solid (0.219 g, 42%).

후처리

  1. customdegassed
  2. customThe reaction was partitioned between EtOAc and saturated aqueous sodium carbonate
  3. customthe organic layer separated
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to dryness
  6. customThe mixture was purified by column chromatography
  7. washeluting with 10% EtOAc/Petroleum ether

출처 및 근거

ORD 기록
ord-778fecfc56b8447383346e117a1a288a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530489B2

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