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

HRID 507355ノート

反応式

HRID 507355 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-65b06e9f616b4ceaaa0736db5df97c6f
出典データセット
uspto-grants-2010_08
特許番号
US07786152B2

反応ノート

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