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

HRID 1945585노트

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HRID 1945585 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

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온도
120 °C

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-d33c3da2a09f4c35973d19352e07c4fa
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394796B2

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