Sodium Carbonate → HCID 135974539, compound

HRID 2054389Notes

Reaction equation

HRID 2054389 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:18](I)=[C:11]2[N:12]=[C:13]([CH3:17])[NH:14][C:15](=[O:16])[N:10]2[N:9]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.CO.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:18]([C:24]2[CH:25]=[CH:26][C:21]([Cl:20])=[CH:22][CH:23]=2)=[C:11]2[N:12]=[C:13]([CH3:17])[NH:14][C:15](=[O:16])[N:10]2[N:9]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 1359745377-(2-Chlorophenyl)-8-iodo-2-methyl-3H-pyrazolo[1,5-a][1,3,5]triazin-4-one

Product 1

HCID 135974539HCID 135974539, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 7-(2-chlorophenyl)-8-iodo-2-methyl-3H-pyrazolo-[1,5-a][1,3,5]triazin-4-one (I-1A-1d; 141 g, 364 mmol) and 4-chlorophenylboronic acid (85.1 g, 544 mmol) in dimethoxyethane (1.4 L) was added 2 M aqueous Na2CO3 (365 ml) and then (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II), dichloromethane complex (5.80 g, 7.17 mmol). The reaction was heated at reflux for 16 hours, cooled, and the organic layer separated and then concentrated under reduced pressure. The residue was dissolved in methyltetrahydrofuran (1.4 L) and washed with 1 M aqueous NaOH (2×700 ml) and 1 M aqueous HCl (700 ml). The solvent was removed, in vacuo, to give a brown solid which was suspendend in methanol (1.2 L). The mixture was concentrated to one-third volume, the solids were collected by vacuum filtration in a course sintered glass funnel, washed with methanol (1 L) and then dried, in vacuo, to afford product I-2A-1a as a light-brown solid (103 g, 76%): +APcI MS (M+1) 371.3; 1H NMR (400 MHz, DMSO-d6) δ 12.73 (s, 1H), 7.54-7.43 (m, 4H), 7.35-7.26 (m, 4H), 2.35 (s, 3H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 16 hours
  3. temperaturecooled
  4. customthe organic layer separated
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in methyltetrahydrofuran (1.4 L)
  7. washwashed with 1 M aqueous NaOH (2×700 ml) and 1 M aqueous HCl (700 ml)
  8. customThe solvent was removed, in vacuo
  9. customto give a brown solid which
  10. concentrationThe mixture was concentrated to one-third volume
  11. filtrationthe solids were collected by vacuum filtration in a course sintered glass funnel
  12. washwashed with methanol (1 L)
  13. customdried, in vacuo
  14. customto afford product

Sources & evidence

ORD record
ord-941fc390f95a40038b8f186c02e445a5
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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