Boron tribromide → HCID 10468741, compound

HRID 1421265Notes

Reaction equation

HRID 1421265 reaction equation
[CH2:1]([C:3]1[C:11]2[N:6]3[C:7](=[CH:14][CH:15]=[C:5]3[C:4]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=1)[CH:8]=[C:9]([O:12]C)[CH:10]=2)[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:1]([C:3]1[C:11]2[N:6]3[C:7](=[CH:14][CH:15]=[C:5]3[C:4]=1[C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[CH:8]=[C:9]([OH:12])[CH:10]=2)[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18780613HCID 18780613, compound

Product 1

HCID 10468741HCID 10468741, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-ethyl-6-methoxy-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine (115 mg, 0.337 mmol) in 3 ml of dichloromethane was cooled to -70° C. and 1.05 ml of a 1M boron tribromide solution in dichloromethane was added. When the addition was complete, the cooling source was removed and the mixture allowed to reach room temperature. The reaction mixture was poured into a stirred mixture of dichloromethane (125 ml) and a saturated sodium hydrogen carbonate solution (125 ml). The pH was adjusted to neutral with a 4M hydrochloric acid solution. The organic phase was separated and the aqueous phase further extracted with dichloromethane. The combined organic phases were dried and evaporated to leave 40 mg (40%) of the title compound as a semi solid substance. 1H-NMR (DMSO-d6, 200 MHz) δ: 1.37 (t, 3H), 3.08 (q, 2H), 6.92-7.00 (m, 3H), 7.44-7.65 (m, 5H), 9.68 (s, 1H), 9.90 (s, 1H). (Compound 4).

Workup

  1. additionWhen the addition
  2. customthe cooling source was removed
  3. customto reach room temperature
  4. additionThe reaction mixture was poured into a stirred mixture of dichloromethane (125 ml)
  5. customThe organic phase was separated
  6. extractionthe aqueous phase further extracted with dichloromethane
  7. customThe combined organic phases were dried
  8. customevaporated

Sources & evidence

ORD record
ord-55805c092d0442f8beaddc2ed905e5cd
Source dataset
uspto-grants-2000_06
Patent number
US06075036

Reaction notes

Loading…