Potassium Carbonate → HCID 59667357, 화합물

HRID 533230노트

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HRID 533230 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:20]2[C:21]([NH2:27])=[N:22][CH:23]=[C:24](Br)[CH:25]=2)=[CH:8][C:9]=1[O:10][CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])[CH3:12])=[O:4].[Cl:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CCO.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>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:20]2[C:21]([NH2:27])=[N:22][CH:23]=[C:24]([C:33]3[CH:32]=[CH:31][CH:30]=[C:29]([Cl:28])[CH:34]=3)[CH:25]=2)=[CH:8][C:9]=1[O:10][CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])[CH3:12])=[O:4]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 596673595-(2-Amino-5-bromo-pyridin-3-yl)-3-[1-(2-chloro-phenyl)-ethoxy]-thiophene-2-carboxylic acid methyl ester

생성물 1

HCID 59667357HCID 59667357, 화합물수율 45%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 1140Toluene용매

실험 절차

5-(2-Amino-5-bromo-pyridin-3-yl)-3-[1-(2-chloro-phenyl)-ethoxy]-thiophene-2-carboxylic acid methyl ester (120 mg, 0.26 mmol, 1.0 Eq.), 3-chlorophenyl boronic acid (44 mg, 0.28 mmol, 1.1 Eq.) and Pd(PPh3)4 (30 mg, 0.03 mmol, 0.1 Eq.) were dissolved in toluene (1.6 mL) and EtOH (0.4 mL). 2M K2CO3 (0.5 mL, 1.0 mmol, 3.0 Eq) and the reaction heated under microwave conditions at 140° C. for 15 minutes. The reaction was partitioned between EtOAc (10 mL) and water (10 mL) and the aqueous phase extracted with EtOAc (3×10 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography (40% EtOAc/petroleum Ether) to give the sub-title compound as an off-white solid (57 mg, 0.11 mmol, 45%); 1H NMR (400 MHz, CDCl3) δ 1.75 (3H, d), 3.94 (3H, s), 5.24 (2H, br s), 5.84 (1H, q), 6.86 (1H, s), 7.01-7.41 (6H, m), 7.48 (1H, s), 7.65 (1H, s), 7.68 (1H, d), 8.24 (1H, d).

후처리

  1. customThe reaction was partitioned between EtOAc (10 mL) and water (10 mL)
  2. extractionthe aqueous phase extracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (40% EtOAc/petroleum Ether)

출처 및 근거

ORD 기록
ord-cfb3c26437974251b36f1501f19a861e
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853244B2

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