Sodium Carbonate → 3,7-Bis-(4-chlorophenyl)-2-(2-chlorophenyl)-pyrazolo[1,5-a]pyrimidine

HRID 348036Notes

Reaction equation

HRID 348036 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[C:10](I)=[C:6]2[N:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)C.O.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>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:10]2[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])=[N:8][N:7]3[C:2]([C:16]4[CH:15]=[CH:14][C:13]([Cl:18])=[CH:12][CH:17]=4)=[CH:3][CH:4]=[N:5][C:6]=23)=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 21083717HCID 21083717, compound

Product 1

HCID 104339283,7-Bis-(4-chlorophenyl)-2-(2-chlorophenyl)-pyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
72 °C

Procedure

A mixture of 7-chloro-2-(2-chlorophenyl)-3-iodopyrazolo[1,5-a]pyrimidine (I-1A-1d; 50 mg, 0.13 mmol), 4-chlorophenylboronic acid (30 mg, 0.19 mmol), Na2CO3 (108 mg, 0.67 mmol), and tetrakis(triphenylphosphine)palladium (15 mg, 0.013 mmol) in ethanol (1 ml) and water (0.23 ml) was degassed (3×) by pulling a vacuum followed by refilling with nitrogen gas. The reaction was heated at 72° C. for 2 hr, cooled to room temperature, and then extracted from water with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), and then concentrated, in vacuo. Purification on a Chromatotron using 20% ethyl acetate in hexanes as eluant afforded compound 14A-1 (17 mg, 30%) as a solid: +ESI MS (M+1) 450.3; 1H NMR (400 MHz, CD2Cl2) δ 8.62 (d, J=4.1 Hz, 1H), 8.01 (d, J=8.7 Hz, 2H), 7.56 (d, J=8.7 Hz, 2H), 7.51–7.36 (m, 6H), 7.28 (d, J=8.7 Hz, 2H), 7.04 (d, J=4.1 Hz, 1H).

Workup

  1. customwas degassed (3×)
  2. temperaturecooled to room temperature
  3. extractionextracted from water with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated, in vacuo
  7. customPurification on a Chromatotron
  8. customafforded compound 14A-1 (17 mg, 30%) as a solid

Sources & evidence

ORD record
ord-ad6bbbad1a24430387cf18f1bec5ada1
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

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