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Sodium Bicarbonate → N-(2-t-Butoxycarbonylaminophenyl)-4-(3-cyanopyridin-2-yl)benzamide

HRID 599518
ノート
印刷プレビュー

反応式

HRID 599518 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].Br[C:34]1[N:41]=[CH:40][CH:39]=[CH:38][C:35]=1[C:36]#[N:37].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:22]=[CH:21][C:20]([C:34]2[C:35]([C:36]#[N:37])=[CH:38][CH:39]=[CH:40][N:41]=2)=[CH:19][CH:18]=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 8171532-Bromopyridine-3-carbonitrileHCID 59830883N-(2-t-Butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

生成物 2

HCID 78922-MethylpentaneHCID 67269547N-(2-t-Butoxycarbonylaminophenyl)-4-(3-cyanopyridin-2-yl)benzamide収率 113.1%

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 (400 mg, 0.913 mmol; prepared as described in international patent publication number wo03/087057, method 13, page 60), 2-bromonicotinonitrile (167 mg, 0.913 mmol), tetrakis(triphenylphosphine)palladium[0] (50 mg, 0.043 mmol), 1,2-dimethoxyethane (4 ml) and a saturated aqueous solution of sodium hydrogen carbonate (2 ml) were stirred at 100° c. under an atmosphere of nitrogen in a microwave for 130 mins. 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 60:40 ethyl acetate: isohexane to afford the title compound as a white solid (214 mg, 57%); nmr spectrum: (dmso-d6) 1.45 (s, 9h), 7.18 (m, 2h), 7.57 (m, 1h), 7.66 (dd, 1h), 8.01 (d, 2h), 8.13 (d, 2h), 8.47 (dd, 1h), 8.73 (s, 1h), 8.98 (d, 1h), 9.97 (s, 1h); mass spectrum: m+h+415.

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 60:40 ethyl acetate

出典と根拠

ORDレコード
ord-5d0f16369bc14700b1d5aae13e74265e
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

読み込み中…

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