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Sodium Bicarbonate → N-(2-t-Butoxycarbonylaminophenyl)-4-(3-cyano-5-formylpyridin-2-yl)benzamide

HRID 599520
ノート
印刷プレビュー

反応式

HRID 599520 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:32])[C:17]1[CH:22]=[CH:21][C:20](B2OC(C)(C)C(C)(C)O2)=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:34]1[C:39]([C:40]#[N:41])=[CH:38][C:37]([CH:42]=[O:43])=[CH:36][N:35]=1.C(=O)([O-])O.[Na+]>COCCOC>[CH3:20][CH2:19][CH2:18][CH:17]([CH3:22])[CH3:16].[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:32])[C:17]1[CH:18]=[CH:19][C:20]([C:34]2[C:39]([C:40]#[N:41])=[CH:38][C:37]([CH:42]=[O:43])=[CH:36][N:35]=2)=[CH:21][CH:22]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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 516892Sodium BicarbonateHCID 197106832-Chloro-5-formylnicotinonitrileHCID 59830883N-(2-t-Butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

生成物 2

HCID 78922-MethylpentaneHCID 86624985N-(2-t-Butoxycarbonylaminophenyl)-4-(3-cyano-5-formylpyridin-2-yl)benzamide収率 101.5%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

N-(2-t-butoxycarbonylaminophenyl)-4-(4,4,5,5,tetramethyl-1,3,2,-dioxaborolan-2-yl)benzamide (1.2 g, 2.74 mmol; prepared as described in international patent publication number wo03/087057, method 13, page 60), 2-chloro-3-cyano-5-formylpyridine [prepared as described in de 4429465 a1 (1996)] (456 mg, 2.74 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(ii)dichloride dichloromethane complex 112 mg, 0.137 mmol), 1,2-dimethoxyethane (12 ml) and a saturated aqueous solution of sodium hydrogen carbonate (6 ml) were stirred at 60° c. under an atmosphere of nitrogen for 7.5 hours. the mixture was allowed to cool before being partitioned between dichloromethane and water. the organics were separated, dried over sodium sulfate, filtered and evaporated. the crude product was purified by chromatography on silica eluting with 30:70 to 40:60 ethyl acetate: isohexane to afford the title compound as a cream solid (615 mg, 51%); nmr spectrum: (dmso-d6) 1.45 (s, 9h), 7.18 (m, 2h), 7.56 (m, 2h), 8.10 (d, 2h), 8.17 (d, 2h), 8.70 (s, 1h), 8.90 (d, 1h), 9.39 (d, 1h), 9.97 (s, 1h), 10.18 (s, 1h); mass spectrum: m+na+ 465.

後処理

  1. temperatureto cool
  2. custombefore being partitioned between dichloromethane and water
  3. customthe organics were separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customthe crude product was purified by chromatography on silica eluting with 30:70 to 40:60 ethyl acetate

出典と根拠

ORDレコード
ord-e204b7b7e0244b8db9bfa581380619a5
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07897778B2

反応ノート

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