Sodium Carbonate → HCID 89580074, compound

HRID 2276804Notes

Reaction equation

HRID 2276804 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([CH:11]=[CH2:12])[N:3]=1.[F:13][C:14]1[CH:35]=[CH:34][C:17]([O:18][C:19]2[CH:24]=[CH:23][C:22](B3OC(C)(C)C(C)(C)O3)=[CH:21][CH:20]=2)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:13][C:14]1[CH:35]=[CH:34][C:17]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:2]3[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([CH:11]=[CH2:12])[N:3]=3)=[CH:21][CH:20]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 666684382-[4-(4-Fluorophenoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 89580117HCID 89580117, compound

Product 1

HCID 89580074HCID 89580074, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
90 °C

Procedure

As shown in Scheme 4, a suspension of 2-chloro-6-vinylpyrimidine-4-carboxylic acid (9) (4.38 g, 0.02 mol), 2-(4-(4-fluorophenoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (22) (7.45 g, 0.02 mol), Na2CO3 (5.3 g, 0.05 mol), and PdCl2(PPh3)2 (Aldrich, 701 mg, 1.0 mmol) in dimethoxy ethane(DME)/EtOH/H2O (500 mL, 2:1:2 ratio) was degassed by repeating with Ar2/vacuum cycles. The mixture was heated at 90° C. for 23 h. Upon cooling to the room temperature, the mixture was poured into DCM. The solids were filtered off and the filtrates were washed with H2O and the aqueous phase was extracted with EtOAc. The combined organic layers were dried with anhydrous MgSO4 and concentrated to give 2-(4-(4-fluorophenoxy)phenyl)-6-vinylpyrimidine-4-carboxylic acid (23) pale yellow oil which was then purified by column chromatography (EtOAc:Hexanes=1:1) to give 6.5 g (82% yield), Rf=0.3 (DCM:MeOH=9:1); LC/MS: m/z=337 [M+H]+.

Workup

  1. customwas degassed
  2. temperatureUpon cooling to the room temperature
  3. additionthe mixture was poured into DCM
  4. filtrationThe solids were filtered off
  5. washthe filtrates were washed with H2O
  6. extractionthe aqueous phase was extracted with EtOAc
  7. dry with materialThe combined organic layers were dried with anhydrous MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d08610e9b18a4749b8b56e24338f84e0
Source dataset
uspto-grants-2015_09
Patent number
US09133131B2

Reaction notes

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