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

HRID 522916
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HRID 522916 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매

1
HCID 9811564Bis(dibenzylideneacetone)palladium촉매

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-727d324dcc8f43dfa3ce010e92ead9f0
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09334269B2

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