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

HRID 911070ノート

反応式

HRID 911070 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ec08aa2da8194aef8b5893c95d109547
出典データセット
uspto-grants-2011_09
特許番号
US08022222B2

反応ノート

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