Potassium Phosphate, Tribasic → HCID 67241901, compound

HRID 335743Notes

Reaction equation

HRID 335743 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH2:3][CH2:2]1.[NH2:16][C:17]1[O:18][CH2:19][C@:20]2([N:37]=1)[C:33]1[CH:32]=[C:31]([OH:34])[C:30]([F:35])=[CH:29][C:28]=1[O:27][C:26]1[C:21]2=[CH:22][C:23](Br)=[CH:24][CH:25]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O>[NH2:16][C:17]1[O:18][CH2:19][C@:20]2([N:37]=1)[C:33]1[CH:32]=[C:31]([OH:34])[C:30]([F:35])=[CH:29][C:28]=1[O:27][C:26]1[C:21]2=[CH:22][C:23]([C:4]2[CH2:3][CH2:2][O:1][CH2:6][CH:5]=2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 58466191HCID 58466191, compound

Product 1

HCID 67241901HCID 67241901, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (276 mg, 1.315 mmol), (S)-2-amino-7′-bromo-3′-fluoro-5H-spiro[oxazole-4,9′-xanthen]-2′-ol (300 mg, 0.822 mmol), potassium phosphate (523 mg, 2.465 mmol) and Cl2Pdbis(di-tert-butyl(phenyl)phosphine) (15.28 mg, 0.025 mmol) in 3 ml of dioxane/water=2:1 was heated at 110° C. microwave for 30 min. The reaction mixture was purified by silica gel chromatography (DCM to DCM/MeOH=100:1 to 100:6) to give (R)-2-amino-7′-(3,6-dihydro-2H-pyran-4-yl)-3′-fluoro-5H-spiro[oxazole-4,9′-xanthen]-2′-ol as a white solid.

Workup

  1. customThe reaction mixture was purified by silica gel chromatography (DCM to DCM/MeOH=100:1 to 100:6)

Sources & evidence

ORD record
ord-8adaa70385df481cadb123207104096f
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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