Sodium Carbonate → HCID 9975720, compound

HRID 968666Notes

Reaction equation

HRID 968666 reaction equation
Br[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:4][N:5]2[C:10]([N:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[CH:9][CH:8]=[N:7][C:6]=12.[F:22][C:23]1[CH:28]=[C:27](B(O)O)[CH:26]=[CH:25][N:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O.ClCCl.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:22][C:23]1[CH:28]=[C:27]([C:2]2[C:3]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:4][N:5]3[C:10]([N:11]4[CH2:15][CH2:14][CH2:13][CH2:12]4)=[CH:9][CH:8]=[N:7][C:6]=23)[CH:26]=[CH:25][N:24]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27833962-Fluoropyridine-4-boronic acidHCID 69490103HCID 69490103, compound

Product 1

HCID 9975720HCID 9975720, compoundYield 32%

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

3-Bromo-2-phenyl-7-pyrrolidin-1-ylpyrazolo[1,5-α]pyrimidine (150 mg, 0.44 mmol) was dissolved in N,N-dimethylformamide (4 mL). To this solution was added dichlorobis(tripenylphosphine)palladium (II) (60 mg, 0.09 mmol), 2-fluoropyridin-4-ylboronic acid (92 mg, 0.66 mmol), sodium carbonate (185 mg, 1.76 mmol) and a few drops of water. The resulting solution was heated at 110° C. for 24 hours. The resulting mixture was diluted with dichloromethane and washed with water. The organic phase was dried over magnesium sulfate, filtered and concentrated. The resulting black residue was purified by silica gel chromatography (ethyl acetate:hexane 1:1) to give 50 mg (32%) of the title compound as a white solid. 1H NMR (CDCl3):δ 8.17 (d, 1H), 8.08 (d, 1H), 7.60 (m, 2H), 7.41 (m, 4H), 7.24 (broad s, 1H), 5.87 (d, 1H), 4.06 (broad s, 4H), 2.07 (broad s, 4H); 19F NMR (CDCl3):δ −-69.34; MS m/z 360 (M+1).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting black residue was purified by silica gel chromatography (ethyl acetate:hexane 1:1)

Sources & evidence

ORD record
ord-0596701467f64d679c0e34267bd5aba4
Source dataset
uspto-grants-2007_12
Patent number
US07304068B2

Reaction notes

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