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 717846노트

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HRID 717846 반응식
[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

참가 물질

4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-480478f457214bb9a7d3e7e592649d6f
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193721B2

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