Cesium carbonate → (2-Boc-amino-pyridin-4-yl)-acetic acid ethyl ester

HRID 911070노트

반응식

HRID 911070 반응식
Cl[C:2]1[CH:7]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:4][N:3]=1.[C:14](=[O:21])([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[NH2:15].C(=O)([O-])[O-].[Cs+].[Cs+]>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].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:17]([O:16][C:14]([NH:15][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:4][N:3]=1)=[O:21])([CH3:20])([CH3:19])[CH3:18]

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 57709236Ethyl 2-(2-chloropyridin-4-yl)acetate

생성물 1

HCID 53419364(2-Boc-amino-pyridin-4-yl)-acetic acid ethyl ester수율 74.1%

시약·촉매·용매 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

A flask was charged with ethyl 2-(2-chloropyridin-4-yl)acetate (20.00 g, 100.2 mmol), tert-butyl carbamate (35.21 g, 300.5 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (2.90 g, 5.01 mmol), tris(dibenzylideneacetone)dipalladium(0) (2.29 g, 2.51 mmol), cesium carbonate (48.96 g, 150 mmol) and THF (400 mL). The mixture was heated at reflux under nitrogen for 24 hours. Upon cooling, the reaction was quenched with 10% ammonium acetate solution and extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried and concentrated. The residue was purified by silica gel chromatography, eluting with 20% ethyl acetate/hexane to yield 20.80 g (72.6% yield) of the desired product as white solid.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux under nitrogen for 24 hours
  3. temperatureUpon cooling
  4. customthe reaction was quenched with 10% ammonium acetate solution
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts were washed with water and brine
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with 20% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-ec08aa2da8194aef8b5893c95d109547
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022222B2

반응 노트

불러오는 중…