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Cesium carbonate → 3-(4-chloropyridin-2-ylamino)-N-methylbenzamide

HRID 522916
ノート
印刷プレビュー

反応式

HRID 522916 の反応式
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.N[C:10]1[CH:19]=[CH:18][C:13]([C:14]([NH:16][CH3:17])=[O:15])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([N:75](C)C)=O>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:75][C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:10]=2)[C:14]([NH:16][CH3:17])=[O:15])[CH:7]=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 5

HCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 335152,4-DichloropyridineHCID 2355164-Amino-N-methylbenzamideHCID 634876Binap, (A+-)-

生成物 1

HCID 673535073-(4-chloropyridin-2-ylamino)-N-methylbenzamide収率 38%

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

実験手順

To a solution of 2, 4-dichloropyridine (0.500 g, 3.39 mmoL) and 4-amino-N-methylbenzamide (0.510 g, 3.39 mmoL) in dimethylacetamide (1 mL) was added cesium carbonate (1.6 g, 5.08 mmoL) and the reaction mixture was degassed for 15 min. Pd2(dba)3 (0.154 g, 0.169 mmol) and BINAP (105 mg, 0.169 mmol) were added and the reaction mixture was irradiated in the microwave at 120° C. for 1 h. Then reaction was quenched with water and extracted with EtOAc (2×50 mL). The organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 3-((4-chloropyridin-2-yl)amino)-N-methylbenzamide (0.300 g, 38%) as a solid. Observed mass (M+1): 262.1

後処理

  1. customthe reaction mixture was degassed for 15 min
  2. customthe reaction mixture was irradiated in the microwave at 120° C. for 1 h
  3. customThen reaction
  4. customwas quenched with water
  5. extractionextracted with EtOAc (2×50 mL)
  6. washThe organic extracts were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customPurification by silica gel column chromatography

出典と根拠

ORDレコード
ord-727d324dcc8f43dfa3ce010e92ead9f0
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09334269B2

反応ノート

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