Potassium Carbonate → methyl 5-methyl-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate

HRID 1845560노트

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HRID 1845560 반응식
Br[C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[S:5][C:6]=1[CH3:7].[CH3:12][N:13]1[C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][CH:15]=[N:14]1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:7][C:6]1[S:5][C:4]([C:8]([O:10][CH3:11])=[O:9])=[CH:3][C:2]=1[C:17]1[N:13]([CH3:12])[N:14]=[CH:15][CH:16]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 49129081-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 18536848Methyl 4-bromo-5-methylthiophene-2-carboxylate

생성물 1

HCID 57826485methyl 5-methyl-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate

시약·촉매·용매 3

HCID 178418851HCID 178418851, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
85 °C

실험 절차

To a 125 mL sealed flask was added methyl 4-bromo-5-methyl-2-thiophenecarboxylate (1.56 g, 6.64 mmol) [Prepared according to the procedure of Preparation 10], 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.67 g, 8.03 mmol) [prepared according to the procedure of Preparation 7], K2CO3 (2.76 g, 19.97 mmol) and Pd(PtBu3)2 (170 mg, 0.33 mmol) in 1,4-Dioxane (27 ml) and water (7 ml). The reaction mixture was heated to 85° C. in a sealed tube for 3 hours, cooled to room temperature and partitioned between H2O and CHCl3. The organic fraction was dried (Na2SO4), adsorbed onto silica and purified via column chromatography (0-15% EtOAc/Hexane). (385 mg, 1.4 mmol, 30%): LC-MS (ES) m/z=237 (M+H)+.

후처리

  1. customTo a 125 mL sealed flask
  2. customPrepared
  3. customprepared
  4. temperaturecooled to room temperature
  5. custompartitioned between H2O and CHCl3
  6. dry with materialThe organic fraction was dried (Na2SO4)
  7. custompurified via column chromatography (0-15% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-1ce0026b63dd477aa4bf32f37f2f68fc
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946278B2

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