Water → 2-ethyl-4-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline

HRID 487418

反応式

HRID 487418 の反応式
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[N:18]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)[N:17]=[N:16][N:15]=1.O.[CH2:29]([C:31]1[CH:40]=[C:39]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][C:46](B3OCC(C)(C)CO3)=[CH:45][CH:44]=2)[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]=1)[CH3:30]>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.C1(C)C=CC=CC=1.CO>[CH2:29]([C:31]1[CH:40]=[C:39]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][C:46]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:14]3[N:18]([C:19]4[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=4)[N:17]=[N:16][N:15]=3)=[CH:45][CH:44]=2)[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]=1)[CH3:30]

参加物

8

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 199357722-(4-[(2-Ethylquinolin-4-yloxy)methyl]phenyl)-5,5-dimethyl-1,3,2-dioxaborinaneHCID 199357905-(2-bromophenyl)-1-(4-nitrophenyl)-1H-tetrazole

生成物 1

HCID 199357842-ethyl-4-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline収率 58.2%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒HCID 1140Toluene溶媒2 回

反応条件

温度
60 °C

実験手順

A mixture of potassium carbonate (1.08 g; 7.8 mmol), 5-(2-bromophenyl)-1-(4-nitrophenyl)-1H-tetrazole (1.16 g; 3.2 mmol) (obtained as described in Procedure A, step (ii)), water (10 ml), toluene (10 ml), and methanol (10 ml) was heated to 60° C. to give a clear solution. Compound H (1.0 g; 2.6 mmol) and tetrakis(triphenylphosphine)palladium (0.06 g; 0.05 mmol) were added and the reaction mixture heated at reflux for 6 hours. The mixture was allowed to cool and further toluene (10 ml) added. The organic phase was separated and the aqueous phase extracted with toluene (2×20 ml). The combined organic phases were evaporated and the resultant solid recrystallised from toluene to give 2-ethyl-4-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline (A) as a solid (0.8 g); m.p. and NMR similar to that of the product of procedure A, part (v).

後処理

  1. customto give a clear solution
  2. temperaturethe reaction mixture heated
  3. temperatureat reflux for 6 hours
  4. temperatureto cool
  5. customThe organic phase was separated
  6. extractionthe aqueous phase extracted with toluene (2×20 ml)
  7. customThe combined organic phases were evaporated
  8. customthe resultant solid recrystallised from toluene

出典と根拠

ORDレコード
ord-64996ab9b2de49d7a0a8cf2743d9201b
出典データセット
uspto-grants-1994_03
特許番号
US05294716

関連ノート

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