Dichloromethane → methyl 6-hydroxy-1H-indole-2-carboxylate

HRID 1171214노트

반응식

HRID 1171214 반응식
ClCCl.[CH3:4][O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([O:17]C)[CH:11]=2)=[O:7].B(Br)(Br)Br>O>[CH3:4][O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([OH:17])[CH:11]=2)=[O:7]

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 688173Methyl-6-methoxy-2-indolecarboxylate

생성물 1

HCID 10535709methyl 6-hydroxy-1H-indole-2-carboxylate수율 85%

시약·촉매·용매 1

HCID 962Water용매

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온도
0 °C

실험 절차

To a dichloromethane (10 mL) solution of 6-methoxy-1H-indole-2-carboxylic acid methyl ester (500 mg, 2.44 mmol) was added boron tribromide (12.2 mL, 12.2 mmol) at −78° C., which was stirred for 50 minutes at 0° C. under nitrogen atmosphere. To the reaction solution was added water at 0° C. followed by extraction with ethyl acetate. The organic layer was washed with sat. NaCl followed by drying over anhydrous magnesium sulfate and filtering. The filtrate was concentrated under a reduced pressure and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the title compound (395 mg, 85%) as a white solid.

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with sat. NaCl
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-a9cc46d590d244bd960aafe109635e17
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829585B2

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