Potassium Carbonate → HCID 10091401, compound

HRID 348033Notes

Reaction equation

HRID 348033 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]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 210837012-(2-Chlorophenyl)-7-ethoxy-3-iodopyrazolo[1,5-a]pyrimidine

Product 1

HCID 10091401HCID 10091401, compoundYield 29.3%

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).

Workup

  1. additionwas added
  2. customdegassed dimethoxyethane (136 ml) and water (34 ml)
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with 1 M aqueous NaOH, 1 M aqueous HCl, and brine
  7. filtrationwere collected by filtration (3.0 g)
  8. customThe solvent was removed, in vacuo
  9. customthe residue was triturated from ethanol

Sources & evidence

ORD record
ord-d9fcd9aa192345aaa38476a81007f129
Source dataset
uspto-grants-2007_02
Patent number
US07176210B2

Reaction notes

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