Boron tribromide → 4-Acetyl-1-ethyl-2-(4-hydroxyphenyl)-6-methoxypyrrolo[2,1,5-cd]indolizine

HRID 1421267노트

반응식

HRID 1421267 반응식
[C:1]([C:4]1[CH:5]=[C:6]2[N:14]3[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][C:13]=13)[C:8]([CH2:17][CH3:18])=[C:7]2[C:19]1[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=1)(=[O:3])[CH3:2].B(Br)(Br)Br.[O-2].[Al+3].[O-2].[O-2].[Al+3]>ClCCl.ClCCl.CO>[C:1]([C:4]1[CH:5]=[C:6]2[N:14]3[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][C:13]=13)[C:8]([CH2:17][CH3:18])=[C:7]2[C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1)(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 25134Boron tribromideHCID 9989226AluminaHCID 187806374-Acetyl-1-ethyl-6-methoxy-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine

생성물 1

HCID 187806064-Acetyl-1-ethyl-2-(4-hydroxyphenyl)-6-methoxypyrrolo[2,1,5-cd]indolizine수율 58%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 21226129Dichloromethane methanol용매2회

실험 절차

A solution of 4-acetyl-1-ethyl-6-methoxy-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine (0.3 g, 0.85 mmol) in 7 ml of dry dichloromethane was cooled to -65° C. and stirred in a nitrogen atmosphere while 1.2 ml of a 1 M boron tribromide solution in dichloromethane was added. Stirring was continued for one hour and the cooling source was removed. The reaction mixture was allowed to reach room temperature and then poured into a stirred medium of dichloromethane (100 ml) and a saturated sodium hydrogen carbonate solution (100 ml). The usual work up afforded 200 mg of a substance which was submitted to column chromatography (aluminium oxide) with dichloromethane/methanol (20:1) as eluent. The fractions having RF 0.4 (silica gel 60, dichloromethane/methanol (20:1)) was collected and evaporated to afford 160 mg (58%) of the title compound. M.p. 245-46° C. 1H-NMR (DMSO-d6, 200 MHz) δ: 1.37 (t, 3H), 2.62 (s, 3H), 3.13 (q, 2H), 4.07 (s, 3H), 7.00 (d, 2H), 7.70 (d, 2H), 7.79 (d, 1H), 7.87 (d, 1H), 8.12 (s, 1H), 9.87 (s, 1H). (Compound 7).

후처리

  1. additionwas added
  2. customthe cooling source was removed
  3. customto reach room temperature
  4. additionpoured into a stirred medium of dichloromethane (100 ml)
  5. customThe usual work up afforded 200 mg of a substance which
  6. customwas collected
  7. customevaporated

출처 및 근거

ORD 기록
ord-9c62228dec544e90a5f977f2d2fbeed6
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06075036

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