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

HRID 711273노트

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HRID 711273 반응식
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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-639dab9b00ec4281908aa8ab772be087
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181235B2

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