Sodium Carbonate → HCID 90310783, compound
Reaction equation
[Si:1]([O:8][C:9]1[C:10]([F:19])=[C:11](B(O)O)[CH:12]=[CH:13][C:14]=1[CH3:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH2:20][C:21]1[CH:26]=[N:25][C:24](Br)=[CH:23][N:22]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[Si:1]([O:8][C:9]1[C:10]([F:19])=[C:11]([C:24]2[N:25]=[CH:26][C:21]([NH2:20])=[N:22][CH:23]=2)[CH:12]=[CH:13][C:14]=1[CH3:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
(3-((tert-Butyldimethylsilyl)oxy)-2-fluoro-4-methylphenyl)boronic acid (292 mg, 1.03 mmol), 2-amino-5-bromopyrazine (179 mg, 1.03 mmol), 1,4-dioxane (6.1 mL), and Na2CO3(2.1 mL, 2 M) were added to a microwave vial and the resultant mixture sparged with argon for 10 minutes. Pd(dppf)Cl2.DCM was then added the mixture, the vial sealed, and then heated at 80° Celsius for 16 hours. The reaction mixture was then cooled to rt, diluted with water (5 mL), and extracted with EtOAc (4×5 mL). The combined organic extracts were then dried over Na2SO4, filtered, and concentrated to dryness to provide the title compound. This compound was used directly in the next synthetic step without purification.
Workup
- customthe resultant mixture sparged with argon for 10 minutes
- additionDCM was then added the mixture
- temperatureThe reaction mixture was then cooled to rt
- additiondiluted with water (5 mL)
- extractionextracted with EtOAc (4×5 mL)
- dry with materialThe combined organic extracts were then dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-e0718e00cbef4937bacca61a3178d12f
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073876B2
Reaction notes
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