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

HRID 1421267Notes

Reaction equation

HRID 1421267 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226129Dichloromethane methanolSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-9c62228dec544e90a5f977f2d2fbeed6
Source dataset
uspto-grants-2000_06
Patent number
US06075036

Reaction notes

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