2-Amino-6-chloro-N-methoxy-N-methyl-nicotinamide → (2-Amino-6-chloro-pyridin-3-yl)-(2-fluoro-phenyl)-methanone

HRID 30105

반응식

HRID 30105 반응식
[NH2:1][C:2]1[N:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:3]=1[C:4](N(OC)C)=[O:5].[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Li]>O1CCCC1>[NH2:1][C:2]1[C:3]([C:4]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[F:15])=[O:5])=[CH:10][CH:11]=[C:12]([Cl:14])[N:13]=1

참가 물질

4

반응물 2

HCID 585908242-Amino-6-chloro-N-methoxy-N-methyl-nicotinamideHCID 178506686HCID 178506686, 화합물

생성물 1

HCID 58590830(2-Amino-6-chloro-pyridin-3-yl)-(2-fluoro-phenyl)-methanone수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

2-Amino-6-chloro-N-methoxy-N-methyl-nicotinamide (500 mg, 2.32 mmol, Example 3) was dissolved in anhydrous tetrahydrofuran (14 mL) and cooled to −78° C. A solution of 2-fluorophenyl lithium (4-6 equiv, freshly prepared following the same procedure as in Example 4) was added. The reaction was stirred at −78° C. for 1-3 hrs and quenched with aqueous ammonium chloride solution. The resulting mixture was extracted with ethyl acetate, washed with saturated sodium chloride, dried over sodium sulfate and evaporated in vacuo. The product was then purified on silica gel to give (2-Amino-6-chloro-pyridin-3-yl)-(2-fluoro-phenyl)-methanone as a white solid (445.5 mg, 77% yield). HRMS, observed: 250.0306, Calcd for M+: 250.0309.

후처리

  1. additionwas added
  2. customquenched with aqueous ammonium chloride solution
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe product was then purified on silica gel

출처 및 근거

ORD 기록
ord-eaad9f2e5822467f90ef726934124adc
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423051B2

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