Potassium Carbonate → 1-Acetyl-6-bromo-5-difluoromethoxyindoline

HRID 3022

反応式

HRID 3022 の反応式
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([OH:14])=[C:10]([Br:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl[C:16]([F:22])([F:21])C(OC)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:14][CH:16]([F:22])[F:21])=[C:10]([Br:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 11430Potassium Carbonate2 回HCID 73935Methyl chlorodifluoroacetate2 回HCID 219483801-(6-Bromo-5-hydroxy-2,3-dihydro-1H-indol-1-yl)ethan-1-one

生成物 1

HCID 196887861-Acetyl-6-bromo-5-difluoromethoxyindoline

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

1-Acetyl-6-bromo-5-hydroxyindoline (2 g, 7.8 mmol), methyl 2-chloro-2,2-difluoroacetate (0.82 ml, 7.8 mmol) and potassium carbonate (1.08 g, 7.8 mmol) were suspended in N,N-dimethylformamide (20 mL) under an argon atmosphere and placed in a 65° C. oil bath. After 3 hr, additional methyl 2-chloro-2,2-difluoroacetate (0.3 ml, 2.8 mmol) and potassium carbonate (0.3 g, 2.2 mmol) was added and heated for 18 hr. The solvent was then removed in vacuo and the residue was partitioned between cold 3N HCl and ether. The aqueous layer was extracted three times with ether, the combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated. The solid was purified by flash chromatography (2% MeOH/CH2Cl2) to provide the title compound as a white solid

後処理

  1. customplaced in a 65° C.
  2. temperatureheated for 18 hr
  3. customThe solvent was then removed in vacuo
  4. customthe residue was partitioned between cold 3N HCl and ether
  5. extractionThe aqueous layer was extracted three times with ether
  6. washthe combined organic extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe solid was purified by flash chromatography (2% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-550474a9556d462983b860f2b003f86a
出典データセット
uspto-grants-1998_03
特許番号
US05731477

関連ノート

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