Potassium Carbonate → (5-{2-[(N-tert-butoxycarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid methyl ester

HRID 554606노트

반응식

HRID 554606 반응식
[C:1]([O:5][C:6](=[O:30])[N:7]([CH2:28][CH3:29])[CH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1B1OC(C)(C)C(C)(C)O1)([CH3:4])([CH3:3])[CH3:2].[CH3:31][O:32][C:33](=[O:42])[CH2:34][C:35]1[CH:36]=[N:37][CH:38]=[C:39](Br)[CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.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>[CH3:31][O:32][C:33](=[O:42])[CH2:34][C:35]1[CH:36]=[N:37][CH:38]=[C:39]([C:10]2[CH:11]=[CH:12][C:13]([C:15]([F:18])([F:16])[F:17])=[CH:14][C:9]=2[CH2:8][N:7]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:30])[CH2:28][CH3:29])[CH:40]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 23398394Methyl 2-(5-bromopyridin-3-yl)acetateHCID 67212456Ethyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzyl]-carbamic acid tert-butyl ester

생성물 1

HCID 67212420(5-{2-[(N-tert-butoxycarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid methyl ester

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

Ethyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzyl]-carbamic acid tert-butyl ester (1.0 g, 2.33 mmol), (5-bromo-pyridin-3-yl)-acetic acid methyl ester (0.535 g, 2.33 mmol), potassium carbonate (0.807 g, 5.8 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.100 g, 0.09 mmol) were combined in DME (8 mL) and H2O (4 mL). The solution was purged with N2, and then the reaction was stirred at 80° C. for 12 hours. The mixture was partitioned between EtOAc and H2O, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography to give (5-{2-[(N-tert-butoxycarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid methyl ester.

후처리

  1. customThe solution was purged with N2
  2. customThe mixture was partitioned between EtOAc and H2O
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-51dc2952ae04487f930bc0a71c7c3791
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08049015B2

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