2-amino-5-bromo-N-methoxy-N-methylnicotinamide → 2-Amino-3-(2-methoxybenzoyl)-5-bromopyridine

HRID 603083

반응식

HRID 603083 반응식
[NH2:1][C:2]1[N:13]=[CH:12][C:11]([Br:14])=[CH:10][C:3]=1[C:4](N(OC)C)=[O:5].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Mg]Br>C1COCC1>[NH2:1][C:2]1[C:3]([C:4]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH3:15])=[O:5])=[CH:10][C:11]([Br:14])=[CH:12][N:13]=1

참가 물질

4

반응물 2

HCID 596997242-amino-5-bromo-N-methoxy-N-methylnicotinamideHCID 178489560HCID 178489560, 화합물

생성물 1

HCID 451083192-Amino-3-(2-methoxybenzoyl)-5-bromopyridine수율 79%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-55 °C

실험 절차

To a flame-dried 100 ml round bottomed flask were added 2-amino-5-bromo-N-methoxy-N-methyl-nicotinamide (661 mg, 2.54 mmol) and anhydrous THF (15 ml). The solution was stirred at −55° C. for 5 minutes under nitrogen, then a 0.5 M solution of 2-methoxyphenyl magnesium bromide in THF (18 ml, 9.0 mmol) was added dropwise over 3 minutes. The resulting solution was allowed to warm to room temperature over 2 hours then quenched by addition of 1 M citric acid (25 ml). Ethyl acetate (50 ml) was added, and the layers were separated. The aqueous fraction was extracted three times with ethyl acetate, and the combined organic fractions were washed with brine, dried (Na2SO4), filtered and concentrated to give a sticky yellow solid. Recrystallization from ethanol provided 619.5 mg (79%) of (2-amino-5-bromo-pyridin-3-yl)-(2-methoxy-phenyl)-methanone as yellow needles. MS m/z: 308 [MH]+.

후처리

  1. temperatureto warm to room temperature over 2 hours
  2. customthen quenched by addition of 1 M citric acid (25 ml)
  3. additionEthyl acetate (50 ml) was added
  4. customthe layers were separated
  5. extractionThe aqueous fraction was extracted three times with ethyl acetate
  6. washthe combined organic fractions were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a sticky yellow solid
  11. customRecrystallization from ethanol

출처 및 근거

ORD 기록
ord-6c19c9453b8047419fdb7e71f4503476
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906648B2

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