Sodium Carbonate → HCID 178418705、化合物

HRID 1370315ノート

反応式

HRID 1370315 の反応式
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.C([O-])(=O)C.[K+].C([O:23][N:24]=[C:25]1[C:33]2([CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[C:32]2[C:27](=[CH:28][CH:29]=[C:30](Br)[CH:31]=2)[NH:26]1)C1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.Cl[Pd]Cl>[OH:23][N:24]=[C:25]1[C:33]2([CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)[C:32]2[C:27](=[CH:28][CH:29]=[C:30]([C:4]3[CH:5]=[C:6]([CH:7]=[C:2]([F:1])[CH:3]=3)[C:8]#[N:9])[CH:31]=2)[NH:26]1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 27833303-Bromo-5-fluorobenzonitrileHCID 178419047HCID 178419047、化合物

生成物 1

HCID 178418705HCID 178418705、化合物収率 66%

試薬・触媒・溶媒 2

HCID 24290Palladium Chloride触媒2 回HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 3-fluoro-5-cyano-bromobenzene (0.4 g, 2.0 mmol) in dry DMF (10 ml) was added diboron pinacolate ester (0.63 g, 2.5 mmol), potassium acetate (0.65 g, 6.7 mmol) and PdCl2 (dppf) (0.2. g) and the reaction was heated to 80° C. under a nitrogen atmosphere. After 8 h. from 5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime) (0.2 g, 0.5 mmol), PdCl2 (dppf) (0.05 g) and sodium carbonate (1.30 g, 12.5 mmol) were added and heating at 80° C. was continued. After 8 h. the reaction was cooled and partitioned between water and ethyl acetate, the organic layer was washed with brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography (SiO2, EtOAc:hexane 1:20) to give the desired product (0.14 g, 0.33 mmol, 66%).

後処理

  1. temperatureheating at 80° C.
  2. temperatureAfter 8 h. the reaction was cooled
  3. custompartitioned between water and ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography (SiO2, EtOAc:hexane 1:20)

出典と根拠

ORDレコード
ord-a7bb6017402e4deaa6f9f9edc126caaf
出典データセット
uspto-grants-2003_06
特許番号
US06583145B1

反応ノート

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