Potassium Carbonate → (R)-2'-(pyridin-3-yl)-7'-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

HRID 1970281Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

0.5-2 ml Microwave vial was charged with (S)-2′-bromo-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (100 mg, 0.244 mmol), pyridin-3-ylboronic acid (38.7 mg, 0.315 mmol), dichlorobis(di-t-butyl-4-dimethylaminophenylphosphine)palladium (II) (7.44 mg, 10.51 μmol) and potassium carbonate (87 mg, 0.630 mmol), dioxane (1 ml) and water (0.12 ml) were added and the vial was sealed and heated at 100° C. in the microwave oven (Biotage) for 1 hr. The mixture was diluted with DCM, filtered through Celite, concentrated and purified by flash chromatography on silica gel (12 g column, 20-100% DCM/MeOH/NH4OH in DCM) to afford (R)-2′-(pyridin-3-yl)-7′-(pyrimidin-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine as yellowish solid.

Workup

additionwere added
customthe vial was sealed
filtrationfiltered through Celite
concentrationconcentrated
custompurified by flash chromatography on silica gel (12 g column, 20-100% DCM/MeOH/NH4OH in DCM)

Sources & evidence

ORD record: ord-428da9793b2742b094a49c13fdfc734a
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426447B2

Reaction notes

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