Sodium Carbonate → HCID 117600617, compound

HRID 1497724Notes

Reaction equation

HRID 1497724 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9](=[O:11])[NH:8][CH:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[CH:18]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:25][C:26]1[C:30](B(O)O)=[C:29]([CH3:34])[O:28][N:27]=1>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:25][C:26]1[C:30]([C:2]2[CH:3]=[CH:4][C:5]3[O:10][C:9](=[O:11])[NH:8][CH:7]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:6]=3[CH:18]=2)=[C:29]([CH3:34])[O:28][N:27]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 117600739HCID 117600739, compound

Product 1

HCID 117600617HCID 117600617, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-Bromo-4-phenyl-3,4-dihydro-benzo[e][1,3]oxazin-2-one (90 mg, 0.296 mmol) in 1,2-dimethoxyethane (3 mL) is added saturated Na2CO3 in water (3 mL), 3,5-dimethylisoxazole-4-boronic acid (90 mg, 0.607 mmol) and Pd(dppf)Cl2 (13.5 mg, 0.016 mml) The mixture is refluxed at 100° C. overnight.

Sources & evidence

ORD record
ord-6dac08a6748142ba8b7d3aaf918fd244
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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