Sodium Carbonate → HCID 86273350, compound

HRID 1497721Notes

Reaction equation

HRID 1497721 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]2[NH:6][C:7](=[O:16])[O:8][CH:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:4]=2[CH:3]=1.[CH3:19][C:20]1[C:24](B(O)O)=[C:23]([CH3:28])[O:22][N:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[CH3:19][C:20]1[C:24]([C:2]2[CH:18]=[CH:17][C:5]3[NH:6][C:7](=[O:16])[O:8][CH:9]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:4]=3[CH:3]=2)=[C:23]([CH3:28])[O:22][N:21]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 117600605HCID 117600605, compound

Product 1

HCID 86273350HCID 86273350, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

6-Bromo-4-phenyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one (150 mg, 0.493 mmol), 3,5-dimethyl-4-isoxazolylboronic acid (208.5 mg, 1.480 mmol), 1,1′-bis(diphenylphosphino)ferocene-palladium(II)dichloride dichloromethane complex (80.5 mg, 0.099 mmol) are added to a microwave vessel. A saturated acqueous solution of sodium carbonate (1 mL) and dimethoxyethane (2 mL) are added. The vessel is purged with argon for 10 min. The reaction mixture is heated in a microwave reactor for 90 minutes. The mixture is filtered and the filter cake is washed with dichloromethane. The volatiles are removed on in vacuo and the residue purified by reversed phase HPLC.

Workup

  1. customThe vessel is purged with argon for 10 min
  2. temperatureThe reaction mixture is heated in a microwave reactor for 90 minutes
  3. filtrationThe mixture is filtered
  4. washthe filter cake is washed with dichloromethane
  5. customThe volatiles are removed on in vacuo
  6. customthe residue purified by reversed phase HPLC

Sources & evidence

ORD record
ord-d5313636f77b4f8194b073603ea59fab
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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