Sodium Carbonate → HCID 67224242, compound

HRID 1257897Notes

Reaction equation

HRID 1257897 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[C:10]([F:17])[CH:9]=1.CC1(C)C(C)(C)OB([C:26]2[CH:27]=[N:28][C:29]([NH2:32])=[N:30][CH:31]=2)O1>O.C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:32][C:29]1[N:30]=[CH:31][C:26]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[C:10]([F:17])[CH:9]=2)=[CH:27][N:28]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 3026814-Bromo-2-fluorobenzoic acidHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol ester

Product 1

HCID 67224242HCID 67224242, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of sodium carbonate (1.4 g, 0.014 mol) in water (8 mL) was added to a mixture of 4-bromo-2-fluorobenzoic acid (1.0 g, 0.0046 mol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (1.5 g, 6.8 mmol), and tetrakis(triphenylphosphine)palladium (0.3 g, 0.2 mmol) in toluene (16 mL) and ethanol (8 mL). The resulting mixture was heated at 120° C. for 15 min. The reaction mixture was washed with ether (3×10 mL) to remove impurity. The aqueous layer was adjusted with 1N HCl to pH 7.0, and purified by RP-HPLC (pH 10) to afford the desired product. LCMS: (M+H)=234.1.

Workup

  1. washThe reaction mixture was washed with ether (3×10 mL)
  2. customto remove impurity
  3. custompurified by RP-HPLC (pH 10)

Sources & evidence

ORD record
ord-5a23867481cf4121a9f6d2d49e2bb70f
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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