Potassium Carbonate → HCID 89633279, 화합물

HRID 1525675노트

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HRID 1525675 반응식
Br[CH2:2][C:3]1[C:15]([Cl:16])=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[C:5]([F:17])[CH:4]=1.[Cl:18][C:19]1[CH:20]=[C:21]([OH:28])[CH:22]=[N:23][C:24]=1[CH:25]1[CH2:27][CH2:26]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Cl:16][C:15]1[C:3]([CH2:2][O:28][C:21]2[CH:22]=[N:23][C:24]([CH:25]3[CH2:27][CH2:26]3)=[C:19]([Cl:18])[CH:20]=2)=[CH:4][C:5]([F:17])=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 580424875-Chloro-6-cyclopropylpyridin-3-OLHCID 86702928HCID 86702928, 화합물

생성물 1

HCID 89633279HCID 89633279, 화합물수율 46%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a stirred solution of tert-butyl 4-(bromomethyl)-5-chloro-2-fluorobenzoate (Preparation 25, 2.50 g, 7.99 mmol) and 5-chloro-6-cyclopropylpyridin-3-ol (Preparation 42 WO2012007869, 1.13 g, 6.66 mmol) in DMSO (25 mL) was added K2CO3 (2.76 g, 19.9 mmol). The resulting mixture was stirred under nitrogen at room temperature for 18 hours. The reaction mixture was then quenched with water (30 mL) and extracted with EtOAc (2×30 mL). The combined organic layers were washed with water (30 mL), dried over MgSO4 and evaporated under reduced pressure to give the crude product (2.69 g). Purification was accomplished by column chromatography on silica (eluting with 1:9 Et2O/cyclohexane) affording the title compound (1.24 g, 46%).

후처리

  1. customThe reaction mixture was then quenched with water (30 mL)
  2. extractionextracted with EtOAc (2×30 mL)
  3. washThe combined organic layers were washed with water (30 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customto give the crude product (2.69 g)
  7. customPurification

출처 및 근거

ORD 기록
ord-04f09de6b24243349d62b830e463d726
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085517B2

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