Sodium Carbonate → HCID 67399195、化合物

HRID 471598

反応式

HRID 471598 の反応式
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]

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 6157276((1E)-prop-1-en-1-yl)boronic acidHCID 24971989HCID 24971989、化合物

生成物 1

HCID 67399195HCID 67399195、化合物収率 94.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f5085f93e9574224a1bdf498b7591d2f
出典データセット
uspto-grants-2014_01
特許番号
US08633186B2

関連ノート

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