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

HRID 30105

反応式

HRID 30105 の反応式
[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

参加物

4

反応物 2

HCID 585908242-Amino-6-chloro-N-methoxy-N-methyl-nicotinamideHCID 178506686HCID 178506686、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-eaad9f2e5822467f90ef726934124adc
出典データセット
uspto-grants-2008_09
特許番号
US07423051B2

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