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

HRID 564478노트

반응식

HRID 564478 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 16079156(1R)-Dicyclohexyl(2'-methoxy-[1,1'-binaphthalen]-2-yl)phosphane촉매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-407aa876ce22447c96c5cd90ff71fa5c
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067408B2

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