Potassium Phosphate, Tribasic → 2-(5-(6-Fluoro-3-methylimidazo[1,2-a]pyridin-2-yl)pyridin-3-yl)propan-2-ol

HRID 705074Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([C:15]([OH:18])([CH3:17])[CH3:16])[CH:12]=[N:13][CH:14]=2)O1.Cl[C:21]1[N:22]=[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][N:24]2[C:30]=1[CH3:31].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:29][C:26]1[CH:27]=[CH:28][C:23]2[N:24]([C:30]([CH3:31])=[C:21]([C:9]3[CH:10]=[C:11]([C:15]([OH:18])([CH3:16])[CH3:17])[CH:12]=[N:13][CH:14]=3)[N:22]=2)[CH:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of the title compound from Example 2 Step D (0.135 g, 0.514 mmol) and the title compound from Example 3 Step B (0.079 g, 0.428 mmol) in tetrahydrofuran (4.28 mL) were added palladium acetate (9.61 mg, 0.043 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (0.035 g, 0.086 mmol), and potassium phosphate tribasic (0.273 g, 1.284 mmol). The resulting mixture was heated at 100° C. for 18 hours, then filtered with the aid of ethyl acetate and concentrated under reduced pressure. Purification by flash chromatography on silica gel (50% acetone in dichloromethane) provided the title compound: LCMS m/z 286.17 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.83 (s, 1H), 8.75 (s, 1H), 8.26 (d, J=2.0 Hz, 1H), 7.85 (s, 1H), 7.63 (dd, J=9.8, 5.1 Hz, 1H), 7.16-7.12 (m, 1H), 2.64 (s, 3H), 2.28 (br s, 1H), 1.67 (s, 6H).

Workup

filtrationfiltered with the aid of ethyl acetate
concentrationconcentrated under reduced pressure
customPurification by flash chromatography on silica gel (50% acetone in dichloromethane)

Sources & evidence

ORD record: ord-8e365d82e3f0480ca520930625c6ec46
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09173873B2

Reaction notes

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