Water → HCID 69059481, 화합물

HRID 2103614노트

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HRID 2103614 반응식
Br[C:2]1[S:3][CH:4]=[C:5]([S:7]([CH3:10])(=[O:9])=[O:8])[CH:6]=1.[F-].[Cs+].[CH:13]1([CH:18]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH2:20][OH:21])[CH2:17][CH2:16][CH2:15][CH2:14]1.O>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:13]1(/[CH:18]=[C:19](\[C:2]2[S:3][CH:4]=[C:5]([S:7]([CH3:10])(=[O:9])=[O:8])[CH:6]=2)/[CH2:20][OH:21])[CH2:17][CH2:16][CH2:15][CH2:14]1

참가 물질

7

반응물 4

HCID 962WaterHCID 25953Cesium fluorideHCID 670847173-Cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-olHCID 674844052-Bromo-4-(methylsulfonyl)thiophene

생성물 1

HCID 69059481HCID 69059481, 화합물

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

Add 2-bromo-4-methanesulfonyl-thiophene (241 mg, 1.0 mmol), caesium fluoride ( 304 mg, 2.0 mmol) and tetrakis-(triphenylphosphin)-palladium(0) (58 mg, 0.05 mmol) to a solution of 3-cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (252 mg, 1.0 mmol) in THF. Stir at 50° C. for 24 h, monitore completion of the reaction by LCMS. Treat the reaction mixture with water and extract with ethyl acetate. Dry organic layers over sodium sulfate and remove solvents under vacuum to obtain 405 mg crude product. Purify by silica gel chromatography, eluting with gradient from 9:1 to 1:1 hexane:ethyl acetate to obtain 118 mg purified product. MS (m/e): 309.0 (M+Na).

후처리

  1. custommonitore completion of the reaction by LCMS
  2. extractionextract with ethyl acetate
  3. customDry organic layers over sodium sulfate and remove solvents under vacuum
  4. customto obtain 405 mg crude product
  5. customPurify by silica gel chromatography
  6. washeluting with gradient from 9:1 to 1:1 hexane
  7. customethyl acetate to obtain 118 mg
  8. custompurified product

출처 및 근거

ORD 기록
ord-c51b99adf5324355a8e16c09c68d36f5
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576108B2

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