Sodium Bicarbonate → ethyl 5-methoxy-4-methyl-1H-indole-2-carboxylate

HRID 515728노트

반응식

HRID 515728 반응식
Br[C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[NH:6]2.[Cl-].C[Zn+].[C:21]([O-])(O)=O.[Na+]>C1COCC1.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>[CH3:12][O:11][C:10]1[C:2]([CH3:21])=[C:3]2[C:7](=[CH:8][CH:9]=1)[NH:6][C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4]2

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 11460715Ethyl 4-bromo-5-methoxy-1H-indole-2-carboxylateHCID 178477797HCID 178477797, 화합물

생성물 1

HCID 21396313ethyl 5-methoxy-4-methyl-1H-indole-2-carboxylate

시약·촉매·용매 2

HCID 178418851HCID 178418851, 화합물촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
65 °C

실험 절차

To a reaction mixture of ethyl 4-bromo-5-methoxy-1H-indole-2-carboxylate (1 g, 3.35 mmol) and bis(tri-t-butylphosphine)palladium (0) (0.171 g, 0.335 mmol) in THF (10 mL) was added a 2 M solution of methylzinc(II) chloride in THF (5.03 mL, 10.06 mmol) at room temperature. The reaction was stirred at 65° C. for 2 h, cooled down, and added saturated aqueous NaHCO3 solution. The solid was filtered off through celite and washed with ethyl acetate. The filtrate was extracted with ethyl acetate. The combined organics were dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica gel column chromatography to give the title compound as white solid (712 mg). LCMS m/z=234.2 [M+H]+; 1H NMR (400 MHz, CDCl3) α ppm 1.42 (t, J=7.1 Hz, 3H), 2.44 (s, 3H), 3.87 (s, 3H), 4.41 (q, J=7.1 Hz, 2H), 7.05 (d, J=9.0 Hz, 1H), 7.19-7.24 (m, 2H), 8.81 (s, 1H).

후처리

  1. temperaturecooled down
  2. filtrationThe solid was filtered off through celite
  3. washwashed with ethyl acetate
  4. extractionThe filtrate was extracted with ethyl acetate
  5. dry with materialThe combined organics were dried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-46fbe6ab6439465c85d3844b6ea2bce5
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108969B2

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