6-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamine → HCID 57512846, compound

HRID 390Notes

Reaction equation

HRID 390 reaction equation
COc1nc(N)ccc1-c1cnn(C)c1.Cc1ccnc(C2CN(C)Cc3ccc(Cl)nc3O2)c1>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(c2cc(C)ccn2)CN(C)C3)ccc1-c1cnn(C)c1

Participants

7

Reactant 2

HCID 575128666-Methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamineHCID 57512930HCID 57512930, compound

Product 1

HCID 57512846HCID 57512846, compoundYield 43.12%

Reagents, catalysts & solvents 4

HCID 23676156Sodium t-butoxideReagentHCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

6-methoxy-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (66.3 mg, 0.32 mmol), 8-chloro-4-methyl-2-(4-methylpyridin-2-yl)-2,3,4,5-tetrahydropyrido[3,2-f][1,4]oxazepine (94 mg, 0.32 mmol), Sodium tert-butoxide (46.8 mg, 0.49 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (20.20 mg, 0.03 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (14.85 mg, 0.02 mmol) were added to a microwave vial then toluene (2 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.

Sources & evidence

ORD record
ord-23ff93d7067c46afbfd708d8d8da4502
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

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