Boron tribromide → 1-[6-ethyl-9-hydroxy-5-(4-hydroxyphenyl)-11-azatricyclo[5.3.1.04,11]undeca-1,3,5,7,9-pentaen-2-yl]ethanone

HRID 1421268Notes

Reaction equation

HRID 1421268 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[N:14]3[C:9](=[CH:10][C:11]([O:15]C)=[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>ClCCl>[C:1]([C:4]1[CH:5]=[C:6]2[N:14]3[C:9](=[CH:10][C:11]([OH:15])=[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

4

Reactant 2

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

Product 1

HCID 1784353781-[6-ethyl-9-hydroxy-5-(4-hydroxyphenyl)-11-azatricyclo[5.3.1.04,11]undeca-1,3,5,7,9-pentaen-2-yl]ethanoneYield 95.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-acetyl-1-ethyl-6-methoxy-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine (0.2 g, 0.58 mmol) in 5 ml of dry dichloromethane was cooled to -65° C. and stirred in a nitrogen atmosphere, while 1.61 ml of a 1M boron tribromide solution in dichloromethane was added. The cooling source was removed and the mixture was stirred for seventy-two hours at room temperature. The mixture was neutralized with a saturated sodium hydrogen carbonate solution. The precipitate was isolated and dried to afford 177 mg (95%) of the title compound. M.p. 274-75° C. 1H-NMR (DMSO-d6, 200 MHz) δ: 1.37 (t, 3H), 2.58 (s, 3H), 3.08 (q, 2H), 7.00 (d, 2H), 7.55 (d, 1H), 7.66 (d, 2H), 7.71 (d, 1H), 8.04 (s, 1H), 9.81 (s, 1H), 10.50 (s, 1H). (Compound 8).

Workup

  1. additionwas added
  2. customThe cooling source was removed
  3. customThe precipitate was isolated
  4. customdried

Sources & evidence

ORD record
ord-4dd0be1fb3014212a2021ba6e7ce5201
Source dataset
uspto-grants-2000_06
Patent number
US06075036

Reaction notes

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