Boron tribromide → 2,3-Dimethyl-7-(o-hydroxyphenacyl)pyrrolo[2,3-b]pyridine

HRID 1756069노트

반응식

HRID 1756069 반응식
[CH3:1][C:2]1[N:21]=[C:5]2[N:6]([CH2:10][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19]C)=[O:12])[CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:22].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][C:2]1[N:21]=[C:5]2[N:6]([CH2:10][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[OH:19])=[O:12])[CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:22]

참가 물질

5

반응물 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 199167932,3-Dimethyl-7-(o-methoxyphenacyl)pyrrolo[2,3-b]pyridine

생성물 1

HCID 199167852,3-Dimethyl-7-(o-hydroxyphenacyl)pyrrolo[2,3-b]pyridine수율 62.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

A solution of 2,3-dimethyl-7-(o-methoxyphenacyl) pyrrolo[2,3-b]pyridine (75 mg, 0.2 mmol) in 20 ml CH2Cl2 was cooled to 0° C. and treated with 1M BBr3 in CH2Cl2 (200 μl, 0.2 mmol). After reacting for an additional hour the reaction mixture was poured into a stirred solution of 5% NaHCO3. The aqueous layer was attracted with 50+10 ml CH2Cl2 and the combined organic layers washed With 50 ml 2M HCl (reextraction trice with 10 ml CH2Cl2). The combined organic layers were dried over MgSO4 and evaporated. The residue was chromatographed (silica, CH2Cl2 /MeOH; 9/1) affording 35 mg (62%) pure title compound.

후처리

  1. waitAfter reacting for an additional hour
  2. washthe combined organic layers washed With 50 ml 2M HCl (reextraction trice with 10 ml CH2Cl2)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customevaporated
  5. customThe residue was chromatographed (silica, CH2Cl2 /MeOH; 9/1)

출처 및 근거

ORD 기록
ord-c70e786a92d341dd9ec1a83bd5eb8a8d
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05439917

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