Potassium Carbonate → HCID 58465943, compound

HRID 1472412Notes

Reaction equation

Br[C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[C:8]([F:24])=[CH:9][C:10]([O:22][CH3:23])=[CH:11][C:12]=3[C@:13]32[N:20]=[C:19]([NH2:21])[CH2:18][O:17][CH2:16]3)=[CH:4][CH:3]=1.[F:25][C:26]1[C:31](B(O)O)=[CH:30][CH:29]=[CH:28][N:27]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[F:24][C:8]1[C:7]2[O:6][C:5]3[C:14](=[CH:15][C:2]([C:31]4[C:26]([F:25])=[N:27][CH:28]=[CH:29][CH:30]=4)=[CH:3][CH:4]=3)[C@:13]3([N:20]=[C:19]([NH2:21])[CH2:18][O:17][CH2:16]3)[C:12]=2[CH:11]=[C:10]([O:22][CH3:23])[CH:9]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A 250 ml RB flask was charged with (S)-7′-bromo-4′-fluoro-2′-methoxy-2,6-dihydrospiro[[1,4]oxazine-3,9′-xanthen]-5-amine (1.0 g, 2.54 mmol), PdCl2(Cy2C6H4NMe2)2 (0.126 g, 0.178 mmol) and 2-fluoropyridin-3-ylboronic acid (0.538 g, 3.81 mmol). Dioxane (12.72 mL) and potassium carbonate (1M solution) (7.63 mL, 7.63 mmol) were added, and the mixture was flushed with argon and heated to 85° C. for 30 min. The mixture was cooled to RT and diluted with EtOAc. The organic layer was separated and concentrated under reduced pressure to give a yellow foam. The residue was purified by chromatography (5-50% of EtOAc/MeOH/NH4OH 90:10:1 in EtOAc) to afford (S)-4′-fluoro-7′-(2-fluoropyridin-3-yl)-2′-methoxy-2,6-dihydrospiro[[1,4]oxazine-3,9′-xanthen]-5-amine (0.82 g, 2.003 mmol, 79% yield).

Workup

customthe mixture was flushed with argon
temperatureThe mixture was cooled to RT
additiondiluted with EtOAc
customThe organic layer was separated
concentrationconcentrated under reduced pressure
customto give a yellow foam
customThe residue was purified by chromatography (5-50% of EtOAc/MeOH/NH4OH 90:10:1 in EtOAc)

Sources & evidence

ORD record: ord-628f2fbae8854ca4951376d1f0ef770c
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012446B2

Reaction notes

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