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6-Hydroxymethylindole → 7-(Cyclopropylamino)-5-[6-(hydroxymethyl)indol-1-yl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 733
Notes
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Reaction equation

HRID 733 reaction equation
N#Cc1cnn2c(NC3CC3)cc(Cl)nc12.OCc1ccc2cc[nH]c2c1>CC(=O)N(C)C.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>N#Cc1cnn2c(NC3CC3)cc(-n3ccc4ccc(CO)cc43)nc12
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 27734596-HydroxymethylindoleHCID 898271735-Chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Product 1

HCID 706927757-(Cyclopropylamino)-5-[6-(hydroxymethyl)indol-1-yl]pyrazolo[1,5-a]pyrimidine-3-carbonitrileYield 47.5%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagent
HCID 636044
1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
Catalyst
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

In a 40mL vial (t=g) was 5-chloro-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (50 mg, 0.21 mmol), [Reactants], and cesium carbonate (77 mg, 0.24 mmol) in DMA (0.5 mL) ([VOLUME]),Pd2(dba)3 (9.80 mg, 10.70 µmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (12.38 mg, 0.02 mmol) were added. to give a brown suspension. The vial was filled with N2, 150C microwave for 30 min. LCMS showed completion. added MeOH (3 mL), filtered through celite. concentrated. The residue was purified by ISCO (Hexane to EtOAc:Hex=1;1 to EtOAc) to give about 34 mg offwhite solid

Sources & evidence

ORD record
ord-e0d4157f08c0492097a16f50798a4aa4
Source dataset
750 AstraZeneca ELN dataset
Original link
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Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes