Tetrahydrofuran → HCID 67416078、化合物

HRID 2192992ノート

反応式

HRID 2192992 の反応式
Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[C:6](Cl)=[N:7]2.C(OC([N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](B(O)O)=[CH:26]1)=O)(C)(C)C.C1C[O:40]CC1>C([O-])([O-])=O.[Na+].[Na+]>[F:17][C:15]1[CH:14]=[CH:13][C:5]2[C:6]([C:27]3[C:28]4[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=4)[NH:25][CH:26]=3)=[N:7][C:8]3[CH:9]=[CH:10][NH:11][C:2](=[O:40])[C:3]=3[C:4]=2[CH:16]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 52330101-(tert-Butoxycarbonyl)indole-3-boronic acidHCID 59375375HCID 59375375、化合物

生成物 1

HCID 67416078HCID 67416078、化合物

試薬・触媒・溶媒 1

HCID 10340Sodium Carbonate溶媒

反応条件

温度
150 °C

実験手順

To a solution of 1,6-dichloro-9-fluorobenzo[c]-1,6-naphthyridine (20 mg, 0.075 mmol) in THF (2 mL) and 2.0 M Na2CO3 (500 μL) were added [1-(tert-butoxycarbonyl)-1H-indol-3-yl]boronic acid (23.5 mg, 0.09 mmol). The solution was degassed by bubbling N2 for 5 min heated to 150° C. for 1 hr in a microwave reactor. The reaction solution was extracted with EtOAc and water, the organic layers were dried with MgSO4, filtered, and concentrated by rotary evaporation. Silcia gel column chromatography with 100% CH2Cl2 to 25% MeOH provided the 9-fluoro-6-(1H-indol-3-yl)benzo[c]-1,6-naphthyridin-1(2H)-one. LRMS (ESI) calc'd for (C20H13FN3O) [M+H]+, 330.1; found 330.1

後処理

  1. customThe solution was degassed
  2. customby bubbling N2 for 5 min
  3. extractionThe reaction solution was extracted with EtOAc and water
  4. dry with materialthe organic layers were dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

出典と根拠

ORDレコード
ord-a9fb2cca65cf4a3691ae162e141238ab
出典データセット
uspto-grants-2012_12
特許番号
US08329722B2

反応ノート

読み込み中…