Water → HCID 58465988, compound

HRID 455722Notes

Reaction equation

HRID 455722 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[F:9][C:10]1[C:15](B(O)O)=[CH:14][CH:13]=[CH:12][N:11]=1.Br[C:20]1[CH:33]=[CH:32][C:31]2[O:30][C:29]3[C:24](=[CH:25][C:26]([O:34][CH2:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:27][CH:28]=3)[C@@:23]3([N:44]=[C:43]([NH2:45])[CH2:42][O:41][CH2:40]3)[C:22]=2[CH:21]=1.O>O1CCOCC1>[CH3:37][C:36]([CH3:39])([CH3:38])[CH2:35][O:34][C:26]1[CH:27]=[CH:28][C:29]2[O:30][C:31]3[C:22](=[CH:21][C:20]([C:15]4[C:10]([F:9])=[N:11][CH:12]=[CH:13][CH:14]=4)=[CH:33][CH:32]=3)[C@:23]3([N:44]=[C:43]([NH2:45])[CH2:42][O:41][CH2:40]3)[C:24]=2[CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27832702-Fluoropyridine-3-boronic acidHCID 58465882HCID 58465882, compound

Product 1

HCID 58465988HCID 58465988, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
135 °C

Procedure

In a microwave vessel, potassium phosphate (0.012 g, 0.056 mmol), bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium(II) (0.985 mg, 1.391 μmol) and 2-fluoropyridin-3-ylboronic acid (5.23 mg, 0.037 mmol) were loaded as solids, and (3R)-2′-bromo-7′-(2,2-dimethylpropoxy)-6H-spiro[1,4-oxazine-3,9′-xanthen]-5-amine (0.008 g, 0.019 mmol) was added via cannula as a solution in dioxane (1 mL). Water (0.25 mL) was added to the vessel, and the mixture was purged with argon gas, then the vessel was sealed and heated in microwave radiation at 135° C. for 30 min. The material was taken up in water (10 mL) and the aqueous phase was extracted with DCM (3×20 mL). The organics were combined, washed with dilute brine (5 mL), dried over sodium sulfate, and concentrated. The material was purified by preparative TLC (13% MeOH/DCM) to afford (3S)-2′-(2,2-dimethylpropoxy)-7′-(2-fluoro-3-pyridinyl)-6H-spiro[1,4-oxazine-3,9′-xanthen]-5-amine.

Workup

  1. customthe mixture was purged with argon gas
  2. customthe vessel was sealed
  3. extractionthe aqueous phase was extracted with DCM (3×20 mL)
  4. washwashed with dilute brine (5 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe material was purified by preparative TLC (13% MeOH/DCM)

Sources & evidence

ORD record
ord-a98fa5c9977442a49197e4b26d5e38b1
Source dataset
uspto-grants-2013_07
Patent number
US08497264B2

Reaction notes

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