Sodium Carbonate → HCID 67399195, 화합물

HRID 471598

반응식

HRID 471598 반응식
I[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[C:4]#[N:5].[CH:13](/B(O)O)=[CH:14]\[CH3:15].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O.CCOC(C)=O>[N+:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:2](/[CH:13]=[CH:14]/[CH3:15])[C:3]=1[C:4]#[N:5])([O-:12])=[O:11]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 6157276((1E)-prop-1-en-1-yl)boronic acidHCID 24971989HCID 24971989, 화합물

생성물 1

HCID 67399195HCID 67399195, 화합물수율 94.2%

시약·촉매·용매 3

HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

A suspension of 2-iodo-6-nitrobenzonitrile (Example 130d) (1.52 g, 5.53 mmol), tetrakis(tiphenylphosphine)palladium(0) (0.64 g, 0.55 mmol), trans-1-propen-1-ylboronic acid (0.95 g, 11.06 mmol), sodium carbonate (0.65 g, 6.08 mmol) and water (10.0 mL) in dimethoxyethane (DME) (40.0 mL) was heated at reflux for 15 h, under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and diluted with water (20 mL) and EtOAc (100 mL). The organic phase was separated and the aqueous phase was extracted with EtOAc (3×50 mL). The combined extract was washed with brine and dried with anhydrous MgSO4. The filtrate was evaporated and the residue was purified by chromatography on silica gel using gradient hexanes to hexanes/EtOAc (7:3), to give 0.98 g (94%) of the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ 8.16-8.24 (m, 2H), 7.83-7.89 (m, 1H), 6.71-6.84 (m, 2H), 1.90-2.02 (m, 3H).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 15 h, under a nitrogen atmosphere
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with EtOAc (3×50 mL)
  5. extractionThe combined extract
  6. washwas washed with brine
  7. dry with materialdried with anhydrous MgSO4
  8. customThe filtrate was evaporated
  9. customthe residue was purified by chromatography on silica gel using gradient hexanes to hexanes/EtOAc (7:3)

출처 및 근거

ORD 기록
ord-f5085f93e9574224a1bdf498b7591d2f
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633186B2

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