Potassium Carbonate → HCID 10091401, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:19](I)=[C:11]2[N:12]=[CH:13][CH:14]=[C:15]([O:16][CH2:17][CH3:18])[N:10]2[N:9]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:19]2[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])=[N:9][N:10]3[C:15]([O:16][CH2:17][CH3:18])=[CH:14][CH:13]=[N:12][C:11]=23)=[CH:24][CH:23]=1Participants
4
Conditions
- Temperature
- 87 °C
Procedure
To a mixture of 2-(2-chlorophenyl)-7-ethoxy-3-iodopyrazolo[1,5-a]pyrimidine (1–11A-1a; 6.76 g, 16.9 mmol), 4-chlorophenylboronic acid (4.07 g, 26.0 mmol), powdered K2CO3 (4.7 g, 34 mmol) and (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II), dichloromethane complex (0.69 g, 0.85 mmol) was added degassed dimethoxyethane (136 ml) and water (34 ml). The reaction was heated at 87° C. for 1.5 hours, cooled, and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with 1 M aqueous NaOH, 1 M aqueous HCl, and brine. Suspended solids were collected by filtration (3.0 g). The solvent was removed, in vacuo, and the residue was triturated from ethanol to give additional solids (1.9 g). The combined solids were purified by silica gel chromatography using 9:1 methylene chloride/ hexanes as eluant to afford 11A-1 (4.45 g, 68%) as an off-white solid: +ESI MS (M+1) 384.3; 1H NMR (400 MHz, CD3OD) δ 8.51 (d, J=5.0 Hz, 1H), 7.53–7.40 (m, 6H), 7.24 (d, J=8.7 Hz, 2H), 6.66 (d, J=5.0 Hz, 1H), 4.59 (q, J=7.1 Hz, 2H), 1.60 (t, J=7.1 Hz, 3H).