Pyridine → Methyl 5-amino-1H-indole-3-carboxylate

HRID 507355노트

반응식

HRID 507355 반응식
ClC1C(C)=C(S(Cl)(=O)=O)C=CC=1.N1C=CC=C[CH:14]=1.COC([C:23]1[NH:24][C:25]2[C:30]([CH:31]=1)=[CH:29][C:28]([NH2:32])=[CH:27][CH:26]=2)=O.[C:33]([O-:36])(O)=[O:34].[Na+]>ClCCl>[CH3:14][O:36][C:33]([C:31]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([NH2:32])[CH:29]=2)[NH:24][CH:23]=1)=[O:34]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 10330149Methyl 5-amino-1H-indole-2-carboxylate

생성물 1

HCID 45089221Methyl 5-amino-1H-indole-3-carboxylate수율 65%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-chloro-2-methylbenzenesulphonyl chloride (124 mg, 0.552 mmol) in dichloromethane (4 mL) was added pyridine (100 μL, 1.3 mmol) and the mixture was stirred under N2 for 5 min, after which time 5-amino-1H-indole-carboxylic acid methyl ester (100 mg, 0.526 mmol) was added. The resulting mixture was stirred for 1.5 h at room temperature, then saturated NaHCO3 solution (15 mL) was added and the mixture was extracted into ethyl acetate (20 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford a white solid (129 mg, 65%), single spot at Rf 0.84 (ethyl acetate). mp 216.8-219.3° C., [22], HPLC purity 99+% (tR 2.07 min in 10% water-acetonitrile). 1H NMR (d6-DMSO): δ 11.91 (1H, s), 10.32 (1H, s), 8.03 (1H, d, J=3.0 Hz), 7.82 (1H, d, J=7.9 Hz), 7.70-7.67 (2H, m), 7.37-7.31 (2H, m), 6.95 (1H, dd, J=8.6, 2.0 Hz), 3.77 (3H, s), 2.65 (3H, s). LCMS: 377.09. FAB-MS (MH+, C17H15ClN2O4S): calcd 378.0441, found 378.0439.

후처리

  1. stirringThe resulting mixture was stirred for 1.5 h at room temperature
  2. extractionthe mixture was extracted into ethyl acetate (20 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue that
  8. customwas purified

출처 및 근거

ORD 기록
ord-65b06e9f616b4ceaaa0736db5df97c6f
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786152B2

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