6-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamine → HCID 57512845, compound
Reaction equation
COc1nc(N)ccc1-c1cnn(C)c1.Cc1ccc(C2CN(C)Cc3ccc(Cl)nc3O2)nc1>CC(C)(C)[O-].Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>COc1nc(Nc2ccc3c(n2)OC(c2ccc(C)cn2)CN(C)C3)ccc1-c1cnn(C)c1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 100 °C
Procedure
6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (0.112 g, 0.55 mmol), 6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (0.112 g, 0.55 mmol), Sodium tert-butoxide (0.079 g, 0.82 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.034 g, 0.05 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (0.025 g, 0.03 mmol) were added to a microwave vial then toluene (3 mL) was added. The reaction mixture was flushed with nitrogen and the mixture was heated to 100°C and stirred overnight. The reaction was complete. The solids were filtered off and washed with DCM. The organic solution was extracted by sat NaHCO3 solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography using DCM : [DCM:MeOH:NH3=90:10:1] = 100:0 to 20:80 as gradient. Yellow foam.
Sources & evidence
- ORD record
- ord-c9c2650e754c4141a34b6871c226f8e2
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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