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Water → 4-(4-bromo-2-methoxyphenyl)-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

HRID 930898
ノート
印刷プレビュー

反応式

HRID 930898 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:18]=[CH:17][N:16](S(C4C=CC(C)=CC=4)(=O)=O)[C:10]=3[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)=[C:4]([O:29][CH3:30])[CH:3]=1.[OH-].[K+].O>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.O1CCOCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:18]=[CH:17][NH:16][C:10]=3[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)=[C:4]([O:29][CH3:30])[CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 867210614-(4-bromo-2-methoxyphenyl)-6-methyl-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one

生成物 1

HCID 867210634-(4-bromo-2-methoxyphenyl)-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one収率 73.2%

試薬・触媒・溶媒 2

HCID 5974Hexadecyltrimethylammonium Bromide触媒
HCID 312751,4-Dioxane溶媒

実験手順

The product from Example 241a (0.2 g, 0.410 mmol), potassium hydroxide (0.460 g, 8.21 mmol) and cetyltrimethylammonium bromide (7.48 mg, 0.021 mmol) were combined in dioxane (8 mL) and water (4 mL) and heated at 100° C. for 18 hours. The reaction mixture was partitioned between equal volumes of ethyl acetate and water and the pH was adjusted to pH 7 by careful addition of concentrated HCl. The organic layer was separated and washed three times with saturated aqueous sodium chloride, dried (Na2SO4), filtered, and concentrated. Purification by trituration in dichloromethane afforded the title compound (0.1 g, 73%). 1H NMR (300 MHz, DMSO-d6) δ ppm 11.97 (s, 1H) 7.05-7.42 (m, 5H) 5.87-6.09 (m, 1H) 3.75 (s, 3H) 3.54 (s, 3H). MS (ESI+) m/z 333/335 (M+H)+.

後処理

  1. customThe reaction mixture was partitioned between equal volumes of ethyl acetate and water
  2. additionthe pH was adjusted to pH 7 by careful addition of concentrated HCl
  3. customThe organic layer was separated
  4. washwashed three times with saturated aqueous sodium chloride
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by trituration in dichloromethane

出典と根拠

ORDレコード
ord-327506b391d94f9681ca7073f937c5b3
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09296741B2

反応ノート

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