Methanol → methyl 2-(5-methoxy-1H-indol-3-yl)acetate

HRID 527441

反応式

HRID 527441 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][C:13]([OH:15])=[O:14].[CH2:16]1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.C(N(CC)CC)C.CO>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][C:13]([O:15][CH3:16])=[O:14]

参加物

6

反応物 4

HCID 887MethanolHCID 8471TriethylamineHCID 189865-Methoxyindoleacetic acidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chloride

生成物 1

HCID 594955methyl 2-(5-methoxy-1H-indol-3-yl)acetate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A reaction mixture containing 2-(5-methoxy-1H-indol-3-yl)acetic acid (0.5 g, 2.44 mmol) and BOP-Cl (0.62 g, 2.44 mmol) in 7 mL of anhydrous CH2Cl2 was treated with triethyl amine (0.49 g, 4.87 mmol) and allowed to stir at ambient temperature for 5 min. The mixture was then combined with anhydrous methanol (0.34 mL) and continuously stirred overnight at room temperature. Following dilution with dichloromethane (30 mL), the organic solution was washed with water (2×15 mL), dried over Na2SO4, and filtered (using a commercial phase separator syringe with attached drying cartridge). The organic filtrate was collected and concentrated in vacuo and the crude ester was purified by flash chromatography on silica gel (ethyl acetate/hexane gradient) to afford the title compound as viscous yellow oil, which permanently crystallized upon storage at −20° C. (453 mg, 85%). C12H13NO3, Mr=219.24; 1H NMR (400 MHz, DMSO-d6) d: 3.60 (s, 3H), 3.70 (s, 2H), 3.74 (s, 3H), 6.72 (dd, J=2.4/8.8 Hz, 1H), 6.96 (d, J=2.4 Hz, 1H), 7.19 (d, J=2.4 Hz, 1H), 7.23 (d, J=8.8 Hz, 1H), 10.77 (s, 1H); LCMS (ESI) tR: 1.95 min (>99%, UV254), m/z: 220.1 [M+1]+.

後処理

  1. washthe organic solution was washed with water (2×15 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered (using a commercial phase separator syringe with attached drying cartridge)
  4. customThe organic filtrate was collected
  5. concentrationconcentrated in vacuo
  6. customthe crude ester was purified by flash chromatography on silica gel (ethyl acetate/hexane gradient)

出典と根拠

ORDレコード
ord-204a741038444dafb862da515d2aac5e
出典データセット
uspto-grants-2016_05
特許番号
US09346803B2

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