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Dimethylformamide → 3-Benzoxazol-2-yl-5-[4-(dimethylaminomethyl)phenyl]pyridin-2-amine

HRID 908368
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HRID 908368 반응식
C(=O)([O-])[O-].[Na+].[Na+].[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]1[C:17]([NH2:23])=[N:18][CH:19]=[C:20](Br)[CH:21]=1.[CH3:24][N:25]([CH2:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)[CH3:26].CN(C=O)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C.O.COCCOC>[O:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]1[C:17]([NH2:23])=[N:18][CH:19]=[C:20]([C:31]2[CH:32]=[CH:33][C:28]([CH2:27][N:25]([CH3:26])[CH3:24])=[CH:29][CH:30]=2)[CH:21]=1
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참가 물질

9

반응물 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 22506610{4-[(Dimethylamino)methyl]phenyl}boronic acidHCID 673880093-(Benzoxazol-2-yl)-5-bromo-pyridin-2-amine

생성물 1

HCID 576871103-Benzoxazol-2-yl-5-[4-(dimethylaminomethyl)phenyl]pyridin-2-amine수율 17.7%

시약·촉매·용매 4

HCID 178418476
HCID 178418476, 화합물
촉매
HCID 702Ethanol용매
HCID 962Water용매
HCID 80711,2-Dimethoxyethane용매

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온도
160 °C

실험 절차

2M Sodium carbonate solution (0.4 ml) was added to a solution of 3-(benzoxazol-2-yl)-5-bromo-pyridin-2-amine (0.10 g), [4-(dimethylaminomethyl)phenyl]boronic acid (0.075 g) and dichlorobis(triphenylphosphine)palladium (II) (0.003 g) in a mixture of 2:7:3:2 DMF:DME:water:ethanol (3 ml). The reaction mixture was heated at 160° C. for 7 mins in a 100 W microwave oven. The solvent was evaporated in a Genevac and NMP (1.8 ml) was added. The mixture was filtered and purified by X bridge preparative HPLC. There was thus obtained the title compound (0.021 g); Mass Spectrum: M+H+ 344, RT 2.82 min.

후처리

  1. customThe solvent was evaporated in a Genevac and NMP (1.8 ml)
  2. additionwas added
  3. filtrationThe mixture was filtered
  4. custompurified by X bridge preparative HPLC

출처 및 근거

ORD 기록
ord-c620512cbeb24ff2b4ec14487e0e5a0c
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08017611B2

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