3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → 3-[6-(4-Fluoro-phenyl)-pyrazolo[1,5-a]pyridin-3-yl]phenylamine

HRID 341239Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([N:14]=[CH:15][C:16]=3I)[CH:13]=2)=[CH:4][CH:3]=1.[NH2:18][C:19]1[CH:20]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:22]=[CH:23][CH:24]=1>COCCOC.C([O-])([O-])=O.[Na+].[Na+]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([N:14]=[CH:15][C:16]=3[C:23]3[CH:24]=[C:19]([NH2:18])[CH:20]=[CH:21][CH:22]=3)[CH:13]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 6-(4-fluoro-phenyl)-3-iodo-pyrazolo[1,5-a]pyridine (140 mg, 0.41 mmol) and 3-aminophenylboronic acid pinacol ester (120 mg, 0.5 mmol) in DME (2 ml) and 2N Na2CO3 (aq, 2 ml) was deoxygenated by evacuation/refill with N2 (×3). PdCl2ddpf (15 mg, 0.02 mmol) was added and the mixture was deoxygenated again (×2). The reaction was stirred and heated at 90° C. under N2 for 24 hours. After cooling to RT the mixture was partitioned between CH2Cl2/H2O. The layers were separated using a phase separating cartridge. The organic layer was evaporated and the residue was purified by chromatography on silica (25→65% EtOAc/Petrol) to give the title compound (55 mg, solid).

Workup

customwas deoxygenated by evacuation/refill with N2 (×3)
additionPdCl2ddpf (15 mg, 0.02 mmol) was added
customthe mixture was deoxygenated again (×2)
temperatureAfter cooling to RT the mixture
customwas partitioned between CH2Cl2/H2O
customThe layers were separated
customseparating cartridge
customThe organic layer was evaporated
customthe residue was purified by chromatography on silica (25→65% EtOAc/Petrol)

Sources & evidence

ORD record: ord-af3c67d7f5bb4bcbbdb8d04041057f06
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895745B2

Reaction notes

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