8-chloro-5-(3-fluorophenyl)-N-methoxy-N-methylimidazo[1,5-a]pyridine-6-carboxamide → 1-[8-Chloro-5-(3-fluorophenyl)imidazo[1,5-a]pyridine-6-yl]propan-1-one

HRID 717846ノート

反応式

HRID 717846 の反応式
[Cl:1][C:2]1[C:3]2[N:4]([CH:21]=[N:22][CH:23]=2)[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[C:6]([C:8](N(OC)C)=[O:9])[CH:7]=1.Cl[Mg][CH2:26][CH3:27]>O1CCCC1>[Cl:1][C:2]1[C:3]2[N:4]([CH:21]=[N:22][CH:23]=2)[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[C:6]([C:8](=[O:9])[CH2:26][CH3:27])[CH:7]=1

参加物

4

反応物 2

HCID 585159348-chloro-5-(3-fluorophenyl)-N-methoxy-N-methylimidazo[1,5-a]pyridine-6-carboxamideHCID 178461633HCID 178461633、化合物

生成物 1

HCID 585159381-[8-Chloro-5-(3-fluorophenyl)imidazo[1,5-a]pyridine-6-yl]propan-1-one収率 49%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of 8-chloro-5-(3-fluorophenyl)-N-methoxy-N-methylimidazo[1,5-a]pyridine-6-carboxamide (300 mg, 0.91 mmol) in tetrahydrofuran (3.0 mL) cooled at 0° C., a 2 M solution of chloro(ethyl)magnesium in tetrahydrofuran (1.6 mL, 3.2 mmol) was added slowly and the mixture was stirred for 3 hours at 0° C. The reaction was quenched with acetic acid (0.5 mL), poured into saturated sodium bicarbonate (25 mL) and extracted with ethyl acetate. The extracts were washed with brine, dried over sodium sulfate, filtered and evaporated. Purification on silica gel using ethyl acetate in hexanes (0-60%) gave the desired compound (130 mg, 49%). LCMS calculated for C16H13ClFN2O (M+H)+: m/z=303.1. found: 302.9.

後処理

  1. customThe reaction was quenched with acetic acid (0.5 mL)
  2. additionpoured into saturated sodium bicarbonate (25 mL)
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customPurification on silica gel

出典と根拠

ORDレコード
ord-480478f457214bb9a7d3e7e592649d6f
出典データセット
uspto-grants-2015_11
特許番号
US09193721B2

反応ノート

読み込み中…