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Phosphorus oxide (P4O10) → 1H-Pyrrolo[2,3-b]pyridine, 4-chloro-5-(5-methoxy-2-oxazolyl)-

HRID 1360183
ノート
印刷プレビュー

反応式

HRID 1360183 の反応式
[Cl:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=O)=[CH:6][N:5]=[C:4]2[NH:16][CH:17]=[CH:18][C:3]=12.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]2[O:13][C:12]([O:14][CH3:15])=[CH:11][N:10]=2)=[CH:6][N:5]=[C:4]2[NH:16][CH:17]=[CH:18][C:3]=12
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 14812Phosphorus oxide (P4O10)HCID 516892Sodium BicarbonateHCID 57928282Glycine, N-[(4-chloro-1H-pyrrolo[2,3-B]pyridin-5-YL)carbonyl]-, methyl ester

生成物 1

HCID 579281581H-Pyrrolo[2,3-b]pyridine, 4-chloro-5-(5-methoxy-2-oxazolyl)-収率 28.9%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To a solution of methyl N-[(4-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)carbonyl]glycinate (167 mg) in chloroform (5 ml) was added diphosphorus pentoxide (886 mg) under ambient temperature, and the mixture was refluxed for 18 hours. The reaction solution was cooled and added to saturated aqueous sodium hydrogencarbonate. The reaction solution was extracted with ethyl acetate. The organic layer was washed with water. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by thin-layer silica gel column chromatography (chloroform:methanol=15:1) to obtain 4-chloro-5-(5-methoxy-1,3-oxazol-2-yl)-1H-pyrrolo[2,3-b]pyridine (45 mg) as a yellowish white solid.

後処理

  1. temperaturethe mixture was refluxed for 18 hours
  2. temperatureThe reaction solution was cooled
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by thin-layer silica gel column chromatography (chloroform:methanol=15:1)

出典と根拠

ORDレコード
ord-9ed005870c4b4cc9913efa7d84fad319
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07879844B2

反応ノート

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