Potassium Phosphate, Tribasic → 1,1-Dimethylethyl {[3'-({[(1,1-dimethylethyl)(dimethyl)silyl]-oxy}methyl)-4-methyl-3-biphenylyl]methyl}carbamate

HRID 662058ノート

反応式

HRID 662058 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:17])=[C:6]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:26][C:27]([Si:30]([CH3:43])([CH3:42])[O:31][CH2:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1)([CH3:29])[CH3:28]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2CCCCC2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2OC)CCCCC1>[CH3:29][C:27]([Si:30]([CH3:43])([CH3:42])[O:31][CH2:32][C:33]1[CH:34]=[C:35]([C:2]2[CH:3]=[CH:4][C:5]([CH3:17])=[C:6]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=2)[CH:36]=[CH:37][CH:38]=1)([CH3:26])[CH3:28]

参加物

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 57813315tert-butyl N-[(5-bromo-2-methylphenyl)methyl]carbamateHCID 57813382[3-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid

生成物 1

HCID 578134201,1-Dimethylethyl {[3'-({[(1,1-dimethylethyl)(dimethyl)silyl]-oxy}methyl)-4-methyl-3-biphenylyl]methyl}carbamate収率 90.6%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 16079156(1R)-Dicyclohexyl(2'-methoxy-[1,1'-binaphthalen]-2-yl)phosphane触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

1,1-Dimethylethyl [(5-bromo-2-methylphenyl)methyl]carbamate (2.7 g, 9.0 mmol), Pd(OAc)2 (81 mg, 0.36 mmol), dicyclohexyl [2′-(methyloxy)-1,1′-binaphthalen-2-yl]phosphane (216 mg, 0.45 mmol) and K3PO4 (2.5 g, 11.7 mmol) were dissolved in dioxane (50 mL). The mixture was heated at 80° C. for 30 min, and then [3-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid (3.1 g, 11.7 mmol) was added. The mixture reaction was stirred at reflux for two days. The solvent was removed under reduced pressure, then diluted with CH2Cl2 (100 mL). The organic layer was washed with water (30 mL), brine (30 mL), and dried over Na2SO4. After removing the solvent, 3.6 g of the crude product 1,1-dimethylethyl {[3′-({[(1,1-dimethylethyl)-(dimethyl)silyl]oxy}methyl)-4-methyl-3-biphenylyl]methyl}carbamate was obtained (yield: 90%).

後処理

  1. customThe mixture reaction
  2. temperatureat reflux for two days
  3. customThe solvent was removed under reduced pressure
  4. additiondiluted with CH2Cl2 (100 mL)
  5. washThe organic layer was washed with water (30 mL), brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. customAfter removing the solvent

出典と根拠

ORDレコード
ord-54527e44b1fc487abbce59e54699379c
出典データセット
uspto-grants-2011_12
特許番号
US08084449B2

反応ノート

読み込み中…