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Water → 4-((3-(2-(2,4-difluorophenoxy)-5-nitrophenyl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl)methyl)morpholine

HRID 633598
ノート
印刷プレビュー

反応式

HRID 633598 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:12]([C:13]3[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=3[O:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[F:30])=[CH:11][N:10]([CH3:31])[C:5]2=[C:6]([O:8][CH3:9])[N:7]=1.[B-](F)(F)(F)[CH2:33][N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.[K+].C([O-])([O-])=O.[Cs+].[Cs+].O>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:30][C:24]1[CH:25]=[C:26]([F:29])[CH:27]=[CH:28][C:23]=1[O:22][C:14]1[CH:15]=[CH:16][C:17]([N+:19]([O-:21])=[O:20])=[CH:18][C:13]=1[C:12]1[C:4]2[C:5](=[C:6]([O:8][CH3:9])[N:7]=[C:2]([CH2:33][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[CH:3]=2)[N:10]([CH3:31])[CH:11]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 45588142Potassium trifluoro[(morpholin-4-yl)methyl]borate(1-)HCID 904161975-bromo-3-(2-(2,4-difluorophenoxy)-5-nitrophenyl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridine

生成物 1

HCID 904168824-((3-(2-(2,4-difluorophenoxy)-5-nitrophenyl)-7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl)methyl)morpholine
収率 52.7%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 218864351,4-Dioxane--water (1/1)溶媒

実験手順

A mixture of Example 182B (110 mg, 0.224 mmol), potassium trifluoro(morpholinomethyl)borate (55.7 mg, 0.269 mmol), palladium (II) acetate (3.02 mg, 0.013 mmol), dicyclohexyl(2′,4′,6′-triisopropyl-[1′,1′-biphenyl]-2-yl)phosphine (12.83 mg, 0.027 mmol), and Cs2CO3 (219 mg, 0.673 mmol) in 4 mL dioxane-water (9:1) was heated under nitrogen in Biotage Initiator microwave oven at 150° C. for 45 minutes. Water was added, extracted with ethyl acetate (2×), washed with water (2×), saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, filtered. The filtrate was concentrated, and the residue was purified by column chromatography on silica gel with a gradient of 0-8% methanol in dichloromethane to give the title compound (60 mg, 0.118 mmol, 52.4% yield).

後処理

  1. extractionextracted with ethyl acetate (2×)
  2. washwashed with water (2×), saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by column chromatography on silica gel with a gradient of 0-8% methanol in dichloromethane

出典と根拠

ORDレコード
ord-a0791008b18b4bae99eb657d2c3e9157
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09321764B2

反応ノート

読み込み中…

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