Toluene → 3-Bromo-6-methoxypyridin-2-amine

HRID 1691836노트

반응식

HRID 1691836 반응식
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[Br:9].[CH3:10][Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C)C=CC=CC=1.S(OC)(OC)(=O)=O>CN(C=O)C>[Br:9][C:3]1[C:2]([NH2:1])=[N:7][C:6]([O:8][CH3:10])=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 1140TolueneHCID 6497Dimethyl SulfateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 178508959HCID 178508959, 화합물

생성물 1

HCID 234358793-Bromo-6-methoxypyridin-2-amine수율 13%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 6-amino-5-bromo-pyridin-2-ol (1.0 g) in DMF (30 mL) was added at 0° C. 0.5 M potassium bis(trimethylsilyl)amide in toluene (11.7 mL, 5.83 mmol) under Ar atmosphere. After stirring for 10 minutes, dimethyl sulfate (0.64 mL, 5.26 mmol) was added at 0° C. The mixture was allowed to warm to room temperature, and was stirred for an additional two hours. Buffer (pH 7) was added and mixture was extracted with diethyl ether. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated to dryness. Purification of the residue by flash chromatography (hexane/toluene 45:55) gave pure 3-bromo-6-methoxy-pyridin-2-ylamine (260 mg, 13% overall).

후처리

  1. stirringwas stirred for an additional two hours
  2. additionBuffer (pH 7) was added
  3. extractionmixture was extracted with diethyl ether
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customPurification of the residue by flash chromatography (hexane/toluene 45:55)

출처 및 근거

ORD 기록
ord-ce2cadbc33ae4ac9b518f9027dcd802b
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153809B2

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