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Acetyl chloride → N-[6-aminopyrid-3-yl]-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide

HRID 1943989
ノート
印刷プレビュー

反応式

HRID 1943989 の反応式
C([NH:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[N:15]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[C:16]3[C:21]([CH:22]=2)=[CH:20][C:19]([F:23])=[CH:18][CH:17]=3)=[O:13])=[CH:7][CH:6]=1)(=O)C.C(Cl)(=O)C>CO.C([O-])(O)=O.[Na+].C(OCC)(=O)C>[NH2:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[N:15]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[C:16]3[C:21]([CH:22]=2)=[CH:20][C:19]([F:23])=[CH:18][CH:17]=3)=[O:13])=[CH:7][CH:6]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 6367Acetyl chlorideHCID 66863369N-[6-(Acetylamino)pyridin-3-yl]-5-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide

生成物 1

HCID 66863527N-[6-aminopyrid-3-yl]-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide収率 85%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒
HCID 516892
Sodium Bicarbonate
溶媒

反応条件

温度
0 °C

実験手順

To a suspension of 0.6 g (1.43 mmol) of N-[6-(acetylamino)pyrid-3-yl]-5-fluoro-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxamide, prepared according to the protocol described in step 4.1, in 9 mL of anhydrous methanol, stirred at 0° C. under an inert atmosphere, are added dropwise 2.03 mL (28.54 mmol) of acetyl chloride. The reaction mixture is stirred at 0° C. for 30 minutes and then gradually brought to 70° C. and stirred for 48 hours. The reaction mixture is concentrated to dryness. The residue obtained is taken up in a mixture of 200 mL of saturated aqueous NaHCO3 solution and 200 mL of ethyl acetate. The phases are separated by settling and the aqueous phase is extracted with 200 mL of ethyl acetate. The combined organic phases are dried over sodium sulfate and then concentrated under reduced pressure. 0.46 g of the expected product is thus obtained.

後処理

  1. customprepared
  2. stirringThe reaction mixture is stirred at 0° C. for 30 minutes
  3. customgradually brought to 70° C.
  4. stirringstirred for 48 hours
  5. concentrationThe reaction mixture is concentrated to dryness
  6. customThe residue obtained
  7. customThe phases are separated
  8. extractionthe aqueous phase is extracted with 200 mL of ethyl acetate
  9. dry with materialThe combined organic phases are dried over sodium sulfate
  10. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-e1a1f2a2b95d4651ad20d0fa440de22d
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08394820B2

反応ノート

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