Sodium Carbonate → HCID 58127115, compound

HRID 1623243Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH:10]2[CH2:15][C@H:14]([CH3:16])[O:13][C@H:12]([CH3:17])[CH2:11]2)[CH:5]=[CH:4][CH:3]=1.[Cl:18][C:19]1[C:20](B(O)O)=[CH:21][C:22]([F:25])=[N:23][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[Cl:18][C:19]1[C:20]([C:2]2[CH:3]=[CH:4][CH:5]=[C:6]([NH:8][CH2:9][CH:10]3[CH2:15][C@H:14]([CH3:16])[O:13][C@H:12]([CH3:17])[CH2:11]3)[N:7]=2)=[CH:21][C:22]([F:25])=[N:23][CH:24]=1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of 6-bromo-N-(((2R,6S)-2,6-dimethyltetrahydro-2H-pyran-4-yl)methyl)pyridin-2-amine (110 mg, 0.36 mmol), 5-chloro-2-fluoro-pyridine-4-boronic acid (193 mg, 1.10 mmol), 0.55 ml 2.0M saturated sodium carbonate aqueous solution in 2 ml DME was purged with Argon for 3 min, PdCl2(dppf)CH2Cl2 (30 mg, 0.037 mmol) was added to this purged. The resulting mixture was heated at about 95° C. in an oil bath for 3.5 hours. Formation of the desired product was confirmed by LCMS: MH+350, 0.70 min. The preceding reaction mixture was diluted with ethyl acetate, washed with water, brine, dried over sodium sulfate and concentrated. The resulting residue was purified by ISCO eluting with 10% ethyl acetate in heptane to give 90 mg desired product as colorless oil. LCMS (m/z): 350 (MH+), retention time=0.70 min.

Workup

customwas purged with Argon for 3 min

Sources & evidence

ORD record: ord-181bc9d893344f438fc0c0a350c2c77d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778951B2

Reaction notes

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