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

HRID 1756069Notes

Reaction equation

HRID 1756069 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-c70e786a92d341dd9ec1a83bd5eb8a8d
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

Loading…