Ethanol → N-(2,4-dimethoxybenzyl)-1-(2',5-dimethyl-3,4'-bipyridin-6-yl)methanamine

HRID 711273ノート

反応式

HRID 711273 の反応式
Br[C:2]1[CH:3]=[C:4]([CH3:21])[C:5]([CH2:8][NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=2[O:19][CH3:20])=[N:6][CH:7]=1.FC1C=C(CN)C=CC=1[C:29]1[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[CH:30]=1.C([O-])([O-])=O.[Na+].[Na+].C(O)C>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(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:20][O:19][C:12]1[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:11]=1[CH2:10][NH:9][CH2:8][C:5]1[N:6]=[CH:7][C:2]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([CH3:35])[CH:30]=2)=[CH:3][C:4]=1[CH3:21]

参加物

8

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 67208674(3-Fluoro-4-(2-methylpyridin-4-yl)phenyl)methanamineHCID 672087031-(5-bromo-3-methylpyridin-2-yl)-N-(2,4-dimethoxybenzyl)methanamine

生成物 1

HCID 67208701N-(2,4-dimethoxybenzyl)-1-(2',5-dimethyl-3,4'-bipyridin-6-yl)methanamine

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

To a round bottom flask was added 1-(5-bromo-3-methylpyridin-2-yl)-N-(2,4-dimethoxybenzyl)methanamine 81-3 (1.5 g, 4.3 mmol), 2-methylpyridin-4-ylboronic acid 15-1 (589 mg, 4.3 mmol), Pd(PPh3)4 (248 mg, 0.22 mmol), saturated Na2CO3 (10 mL), ethanol (10 mL) and toluene (30 mL). The reaction was refluxed at 120° C. for 30 hours. After cooling to room temperature, the reaction was diluted into ethyl acetate and washed with brine. The solvent was removed by rotary evaporation. The crude product was purified by silica gel flash chromatography to give N-(2,4-dimethoxybenzyl)-1-(2′,5-dimethyl-3,4′-bipyridin-6-yl)methanamine 81-4. MS m/z 364.2 (M+1).

後処理

  1. temperatureAfter cooling to room temperature
  2. washwashed with brine
  3. customThe solvent was removed by rotary evaporation
  4. customThe crude product was purified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-639dab9b00ec4281908aa8ab772be087
出典データセット
uspto-grants-2015_11
特許番号
US09181235B2

反応ノート

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