Phosphorus oxybromide → 4-Bromo-6-methyl-1H-pyrrolo[3,2-c]pyridine

HRID 1922735Notes

Reaction equation

HRID 1922735 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](O)[C:5]2[CH:9]=[CH:10][NH:11][C:4]=2[CH:3]=1.P(Br)(Br)([Br:14])=O.C([O-])(O)=O.[Na+]>>[Br:14][C:6]1[C:5]2[CH:9]=[CH:10][NH:11][C:4]=2[CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

4

Reactant 3

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 178422353HCID 178422353, compound

Product 1

HCID 596053264-Bromo-6-methyl-1H-pyrrolo[3,2-c]pyridineYield 12%

Conditions

Temperature
120 °C

Procedure

A mixture of 6-methyl-1H-pyrrolo[3,2-c]pyridin-4-ol (J. Het. Chem., 1996, 303) (161 mg, 1.09 mmol) and phosphorus oxybromide (1.87 g, excess) was heated in a sealed tube at 120° C. for 50 minutes. The reaction mixture was poured onto water (10 mL), basified with aqueous NaHCO3 to pH 8 and the organic product extracted into DCM. The organic layer was dried (phase separator), evaporated and the residue purified by column chromatography (Si—PCC, cyclohexane:ethyl acetate, gradient 100:0 to 70:30) to give 4-bromo-6-methyl-1H-pyrrolo[3,2-c]pyridine (20 mg, 12%) as a white solid. LCMS RT=2.00 min, [M+H]+ 211

Workup

  1. additionThe reaction mixture was poured onto water (10 mL)
  2. extractionthe organic product extracted into DCM
  3. customThe organic layer was dried (phase separator)
  4. customevaporated
  5. customthe residue purified by column chromatography (Si—PCC, cyclohexane:ethyl acetate, gradient 100:0 to 70:30)

Sources & evidence

ORD record
ord-7214f68893fc4057828deda0b5328e10
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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