Potassium Phosphate, Tribasic → (S)-1-(2-amino-2'-(pyridin-3-yl)-5H-spiro[oxazole-4,9'-xanthene]-7'-yl)-4-hydroxybutan-1-one

HRID 335775

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]=[CH: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.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[O:35]1[CH2:39][CH2:38][CH:37]=[C:36]1B1OC(C)(C)C(C)(C)O1.CC(N)CC1C=CC=CC=1.[OH:59]P(O)(O)=O>C(OCC)(=O)C.O.O1CCOCC1>[NH2:26][C:23]1[O:24][CH2:25][C@:5]2([N:22]=1)[C:6]1[CH:7]=[C:8]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH:9]=[CH:10][C:11]=1[O:12][C:13]1[C:4]2=[CH:3][C:2]([C:37](=[O:36])[CH2:38][CH2:39][CH2:35][OH:59])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A 2-5 ml microwave vial was charged with (S)-2′-bromo-7′-(pyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (96 mg, 0.235 mmol), potassium phosphate (150 mg, 0.705 mmol), 2-(4,5-dihydrofuran-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (92 mg, 0.470 mmol) and AmPhos (16.65 mg, 0.024 mmol). 1,4-Dioxane (1176 μL) and water (392 μL) were added and the vial was sealed and heated in microwave reactor for 1 hr at 100° C. The mixture was diluted with ethyl acetate, filtered through celite, and concentrated on 2 g of silica gel. Purification by flash chromatography on 12 g rediSep column using 5-50% gradient of DCM/MeOH/NH4OH (90:10:1) in DCM provided (S)-1-(2-amino-2′-(pyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthene]-7′-yl)-4-hydroxybutan-1-one as an off-white solid.

Workup

customthe vial was sealed
filtrationfiltered through celite
concentrationconcentrated on 2 g of silica gel
customPurification by flash chromatography on 12 g rediSep column

Sources & evidence

ORD record: ord-5dd16a8a43e847e6a4b72a066986b6fc
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883782B2

Linked notes

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