Dichloromethane → HCID 21880576, compound

HRID 899323Notes

Reaction equation

HRID 899323 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[N:10]=[C:11]3[C:16](=[O:17])[N:15]([CH2:18][C:19]([F:22])([F:21])[F:20])[C:14]([CH3:23])=[N:13][C:12]=23)=[CH:4][CH:3]=1.[CH2:31](B(O)O)[CH2:32][CH2:33][CH3:34].C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>C1COCC1.O>[CH2:31]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[N:10]=[C:11]3[C:16](=[O:17])[N:15]([CH2:18][C:19]([F:20])([F:22])[F:21])[C:14]([CH3:23])=[N:13][C:12]=23)=[CH:4][CH:3]=1)[CH2:32][CH2:33][CH3:34]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 20479Butylboronic AcidHCID 11363997HCID 11363997, compound

Product 1

HCID 21880576HCID 21880576, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(4-bromophenyl)-2-(2-chlorophenyl)-5-methyl-6-(2,2,2-trifluoroethyl)-2,6-dihydropyrazolo[4,3-d]pyrimidin-7-one (4A-9, 48.4 mg, 0.1 mmol), 1-butane boronic acid (12 mg, 0.12 mmol), K2CO3 (41 mg, 0.3 mmol), PdCl2dppf.CH2Cl2 (8 mg, 0.01 mmol) in THF (2 ml) was heated at 65° C. for 18 h. The reaction mixture was cooled to room temperature, diluted with H2O, and extracted with EtOAc (2×). The combined extracts were washed with 0.5 M citric acid, saturated aqueous NaCl, dried, and concentrated under vacuum. The crude residue was purified on a Chromatotron using 1 mm plates and 25% EtOAc/hexanes as a solvent to give 8A-1 (16 mg): MS (m/z) 475.5 (M+H)+; 1H NMR (400 MHz, CDCl3): δ 7.53-7.49 (m, 1H), 7.47-7.36 (m, 3H), 7.31 (d, J=8.3 Hz, 2H), 7.12 (d, J=8.3 Hz, 2H), 4.98-4.78 (br m, 2H), 2.60 (s, 3H), 2.56 (t, J=7.5 Hz, 2H), 1.6-1.5 (m, 2H), 1.36-1.27 (m, 2H), 0.89 (t, J=7.5 Hz, 3H).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined extracts were washed with 0.5 M citric acid, saturated aqueous NaCl
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customThe crude residue was purified on a Chromatotron
  6. customto give 8A-1 (16 mg)

Sources & evidence

ORD record
ord-2208be1e82884b05b9e7eafb8479e52e
Source dataset
uspto-grants-2008_04
Patent number
US07354929B2

Reaction notes

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