Acetyl chloride → Acetic acid 7-allyl-1H-indazol-6-yl ester

HRID 2121857ノート

反応式

HRID 2121857 の反応式
[CH2:1]([C:4]1[C:5]([OH:13])=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][N:10]=[CH:9]2)[CH:2]=[CH2:3].C(N(CC)CC)C.[C:21](Cl)(=[O:23])[CH3:22]>C1COCC1>[CH2:1]([C:4]1[C:5]([O:13][C:21](=[O:23])[CH3:22])=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][N:10]=[CH:9]2)[CH:2]=[CH2:3]

参加物

5

反応物 3

HCID 6367Acetyl chloride3 回HCID 8471TriethylamineHCID 1358436477-Allyl-1H-indazol-6-ol

生成物 1

HCID 69566045Acetic acid 7-allyl-1H-indazol-6-yl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of the product from Step B (6.35 g, 37 mmol) in THF (100 mL) containing triethylamine (7.6 ml, 55 mmol) was stirred for 5 minutes at ambient temperature, cooled to 0° C. (ice bath), and acetyl chloride (2.63 mL, 37 mmol) was added. The mixture was stirred at 0° C. for 2 hours, additional acetyl chloride (0.26 mL, 3.7 mmol) was added, and the mixture stirred for 10 min at which point another portion of acetyl chloride (0.26 ml, 3.7 mmol) was added and stirring continued for 15 min. The reaction was quenched with triethyl amine (1 mL) and saturated aqueous sodium bicarbonate (100 mL) and extracted with ethyl acetate (100 mL). The extract was dried (MgSO4) and evaporated to an oil (9.27 g) which was purified by chromatography (silica, 10% to 50% EtOAc/hexane) to give a white solid, (3.50 g, 44%): LC/MS (+APCI) m/z 217 (M+H).

後処理

  1. additionwas added
  2. stirringThe mixture was stirred at 0° C. for 2 hours
  3. additionwas added
  4. stirringstirring
  5. waitcontinued for 15 min
  6. customThe reaction was quenched with triethyl amine (1 mL) and saturated aqueous sodium bicarbonate (100 mL)
  7. extractionextracted with ethyl acetate (100 mL)
  8. dry with materialThe extract was dried (MgSO4)
  9. customevaporated to an oil (9.27 g) which
  10. customwas purified by chromatography (silica, 10% to 50% EtOAc/hexane)
  11. customto give a white solid, (3.50 g, 44%)

出典と根拠

ORDレコード
ord-dd3c88a898294c168d54ab848edfed13
出典データセット
uspto-grants-2004_02
特許番号
US06696476B2

反応ノート

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