Methanol → Methyl 2-(4-(4-amino-2-methyl-1H-indol-5-yloxy)-2,3-dimethylphenyl)acetate

HRID 2423289노트

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HRID 2423289 반응식
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][C:10]2[C:11]([N+:20]([O-])=O)=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][C:14]([CH3:19])=[CH:13]3)[CH:5]=[CH:4][C:3]=1[CH2:23][C:24]([OH:26])=[O:25].O.O.[Sn](Cl)(Cl)(Cl)Cl.[CH3:34]O>C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[NH2:20][C:11]1[C:10]([O:9][C:6]2[CH:5]=[CH:4][C:3]([CH2:23][C:24]([O:26][CH3:34])=[O:25])=[C:2]([CH3:1])[C:7]=2[CH3:8])=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[C:14]([CH3:19])[NH:15]2

참가 물질

6

반응물 3

HCID 887MethanolHCID 598648942-(2,3-Dimethyl-4-(2-methyl-4-nitro-1H-indol-5-yloxy)phenyl)acetic acidHCID 85782573Tin tetrachloride dihydrate

생성물 1

HCID 59864869Methyl 2-(4-(4-amino-2-methyl-1H-indol-5-yloxy)-2,3-dimethylphenyl)acetate

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

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온도
60 °C

실험 절차

Under an N2 atmosphere, 2-(2,3-dimethyl-4-(2-methyl-4-nitro-1H-indol-5-yloxy)phenyl)acetic acid (0.335 g, 0.946 mmol) was suspended in methanol and tin chloride dihydrate (1.71 g, 7.57 mmol) was added. The reaction was heated to 60° C. for 16 h. The reaction was diluted with ethyl acetate and 10% NaHCO3 (aq). The layers were separated and the organic layer was washed with water (3×), dried (Na2SO4), filtered and concentrated in vacuo. Flash column chromatography of the residue, eluting with 20% to 80% ethyl acetate in hexanes, afforded the title compound. LC-MS ESI (pos.) m/z: 339.2 (M+H).

후처리

  1. customThe layers were separated
  2. washthe organic layer was washed with water (3×)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washFlash column chromatography of the residue, eluting with 20% to 80% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-b404200bf81e48bc8374df64ba8ecc2c
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960567B2

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