Toluene → N-(6-Methyl-4'-nitrobiphenyl-3-yl)-3-(trifluoromethyl)benzamide

HRID 77704

反応式

HRID 77704 の反応式
I[C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:21])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].CC1(C)C(C)(C)OB([C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=2)O1.C1(C)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[CH3:8][C:7]1[C:2]([C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=2)=[CH:3][C:4]([NH:9][C:10](=[O:21])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[CH:5][CH:6]=1

参加物

7

反応物 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 27735554,4,5,5-Tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolaneHCID 7925506N-(3-iodo-4-methylphenyl)-3-(trifluoromethyl)benzamide

生成物 1

HCID 69273794N-(6-Methyl-4'-nitrobiphenyl-3-yl)-3-(trifluoromethyl)benzamide収率 95.79%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

To N-(3-iodo-4-methylphenyl)-3-(trifluoromethyl)benzamide (400.0 mg, 0.99 mmol) was added 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane (270 mg, 1.1 mmol) followed by toluene (8.2 mL), then ethanol (1.15 mL), and K2CO3 (270 mg, 2.0 mmol in 1.1 mL water). The reaction was degassed with N2, then tetrakis(triphenylphosphine)palladium(0) (60 mg, 0.05 mmol) was added. The reaction was degassed again, and then heated at reflux under N2 atmosphere at 90° C. until LCMS and TLC indicated complete reaction, about 16 hours. The reaction was then cooled to ambient temperature, transferred to a separatory funnel and partitioned between water and EtOAc. The phases were separated and the organic phase was washed with water, then saturated aqueous NaCl, dried (MgSO4) and then evaporated to dryness to leave the crude product, which was purified by column chromatography to give the product (379 mg, 95.79%). 1H NMR (400 MHz, CDCl3): δ 8.29 (m, 2H), 8.12 (s, 1H), 8.07 (d, 1H), 7.82 (m, 2H), 7.5-7.7 (m, 5H), 7.33 (d, 1H), 2.26 (s, 3H). MS (EI) m/z=401 (M+H).

後処理

  1. customThe reaction was degassed with N2
  2. customThe reaction was degassed again
  3. temperatureheated
  4. customreaction, about 16 hours
  5. temperatureThe reaction was then cooled to ambient temperature
  6. customtransferred to a separatory funnel
  7. custompartitioned between water and EtOAc
  8. customThe phases were separated
  9. washthe organic phase was washed with water
  10. dry with materialsaturated aqueous NaCl, dried (MgSO4)
  11. customevaporated to dryness
  12. customto leave the crude product, which
  13. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-69454351d2e542d88930c953ea7431b2
出典データセット
uspto-grants-2014_09
特許番号
US08841318B2

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