Nitrogen → (3-Imidazo[1,2-a]pyridin-3-yl-phenyl)-pyridin-3-yl-amine

HRID 1093522Notes

Reaction equation

[N:1]1[CH:2]=[C:3]([C:10]2[CH:11]=[C:12]([NH2:16])[CH:13]=[CH:14][CH:15]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.Br[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1.CC([O-])(C)C.[Na+].N#N>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N:1]1[CH:2]=[C:3]([C:10]2[CH:11]=[C:12]([NH:16][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:13]=[CH:14][CH:15]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture 3-imidazo[1,2-a]pyridin-3-yl-phenylamine (315 mg, 1.5 mmol), 3-bromopyridine (160 μl, 1.66 mmol), (±)-Binap (93 mg, 0.15 mmol), and NaOtBu (440 mg, 4.6 mmol) in dry dioxane (3 ml) was deoxygenated by evacuation/refill with N2 (×3). Pd2 dba3 (70 mg, 0.08 mmol) was added and the mixture was deoxygenated again (×3). The reaction was stirred and heated at 100° C. for 18 hours under N2. The mixture was partitioned between EtOAc/H2O, then filtered. The aqueous layer was extracted with EtOAc (×2). The combined extracts were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography to give the title compound. MS: [M+H]+ 287

Workup

customthe mixture was deoxygenated again (×3)
customThe mixture was partitioned between EtOAc/H2O
filtrationfiltered
extractionThe aqueous layer was extracted with EtOAc (×2)
dry with materialThe combined extracts were dried (MgSO4)
filtrationfiltered
customevaporated
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-f829a3cf58bd4ae78c2ae73e3cda2b28
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08131527B1

Reaction notes

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