Piperazine → HCID 67083942, compound
Reaction equation
C1CNCCN1.Cc1ccc(Nc2c(C#N)nnc3cc(Br)ccc23)c(F)c1>CC(=O)N(C)C.CC(C)(C)[O-].CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.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]>Cc1ccc(Nc2c(C#N)nnc3cc(N4CCNCC4)ccc23)c(F)c1Participants
7
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 100 °C
Procedure
A 1L flask was charged with 7-bromo-4-(2-fluoro-4-methylphenylamino)cinnoline-3-carbonitrile (3.93 g, 11.00 mmol), Piperazine (3.88 ml, 49.51 mmol), Tris(dibenzylideneacetone)dipalladium (0) (0.806 g, 0.88 mmol), 2-Dicyclohexylphosphino-2',4',6'-tri-iso-propyl-1,1'-biphenyl (0.787 g, 1.65 mmol) and Sodium tert-butoxide (3.37 ml, 27.51 mmol). The atmosphere was evacuated and replaced with N2(g) and DMA (157 ml) was added to the mixture. The reaction mixture was stirred at 100 °C for 1h. The reaction mixture was cooled to rt, adsorbed on silica gel and flash chromatography using DCM to DCM/MeOH/NH4OH (10:1:0.1) provided the desired adduct as a light brown solid.
Sources & evidence
- ORD record
- ord-b790a1db0b324eea8d1b75eaa501512c
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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