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

HRID 908368Notes

Reaction equation

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

Participants

Conditions

Temperature: 160 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-c620512cbeb24ff2b4ec14487e0e5a0c
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

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