Water → 5-(4-Chloro-phenyl)-6-(2-methoxy-ethoxy)-nicotinic acid methyl ester

HRID 1159198노트

반응식

HRID 1159198 반응식
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8](Br)[C:7]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[N:6][CH:5]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1.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(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:21]2[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=2)[C:7]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[N:6][CH:5]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 675049645-Bromo-6-(2-methoxy-ethoxy)-nicotinic acid methyl ester

생성물 1

HCID 675049675-(4-Chloro-phenyl)-6-(2-methoxy-ethoxy)-nicotinic acid methyl ester수율 56.8%

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

5-Bromo-6-(2-methoxy-ethoxy)-nicotinic acid methyl ester (8.7 g, 29 mmol) was dissolved in toluene (85 mL). To this solution was added with stirring [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) CH2Cl2 (1.2 g, 1.4 mmol), 4-chlorophenylboronic acid (4.9 g, 29 mmol) and sodium carbonate solution (2M, 30 mL). This mixture was heated to 90° C. for 1.5 h and cooled to room temperature. Water (150 mL) was added, the phases were separated and the water mixture was extracted with ethylacetate. Organic phases were pooled, dried with MgSO4 and the volatiles removed in vacuo. The residue was purified by flash chromatography on silica (heptane/ethylacetate, 1:3) to give the title compound (5.3 g) as a pinkish solid; MS (ISP) 322.1 (M+H)+.

후처리

  1. temperaturecooled to room temperature
  2. customthe phases were separated
  3. extractionthe water mixture was extracted with ethylacetate
  4. dry with materialdried with MgSO4
  5. customthe volatiles removed in vacuo
  6. customThe residue was purified by flash chromatography on silica (heptane/ethylacetate, 1:3)

출처 및 근거

ORD 기록
ord-40168f84a6f14601b869d3b03d981550
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812028B2

반응 노트

불러오는 중…