Potassium Phosphate, Tribasic → HCID 57863432, compound

HRID 1446735Notes

Reaction equation

HRID 1446735 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=4)=[O:19])=[CH:13][CH:12]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1.[N:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].O1CCOCC1.O>[N:31]1[CH:36]=[CH:35][C:34]([C:2]2[CH:7]=[CH:6][N:5]3[C:8]([C:11]4[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]5[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:29])([F:30])[F:28])[CH:22]=5)=[O:19])=[CH:13][CH:12]=4)=[CH:9][N:10]=[C:4]3[CH:3]=2)=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2734379(Pyridin-4-yl)boronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 68543228HCID 68543228, compound

Product 1

HCID 57863432HCID 57863432, compoundYield 22.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Load in a 5 mL septum capped vial the following: small magnetic stir bar, 1-[4-(7-chloro-imidazo[1,2-a]pyridin-3-yl)-phenyl]-3-(3-trifluoromethyl-phenyl)-urea (250 mg, 0.58 mmol), 4-pyridyl boronic acid (77.4 mg, 0.63 mmols, 1.1 Eq), S-phos (236 mg), Pd(OAc)2 (60 mg), K3PO4 (237 mg, 1.12 mmol), 1,4-dioxane: H2O 2:1. Heat the reaction to 50° C. for 24 hours, cool and purify with a Varian SCX® (10 g) column that is pre-washed with water and methanol, and elute the product with 2 N NH3 in methanol. Evaporate the product containing fractions under reduced pressure and take up into CH2Cl2 and chromatograph using SiO2 eluting with a gradient of 0% to 10% of 2 M NH3 in MeOH with the balance CH2Cl2. Evaporate the fractions containing the product under reduced pressure, then vacuum oven dry at 40° C. to give the title compound as a yellow solid 61.8 mg (22.5%). MS (ES), m/z 474 (M+1).

Workup

  1. temperatureHeat
  2. customthe reaction to 50° C. for 24 hours
  3. temperaturecool
  4. custompurify with a Varian SCX® (10 g) column that
  5. washis pre-washed with water and methanol
  6. washelute the product with 2 N NH3 in methanol
  7. customEvaporate the product
  8. additioncontaining fractions under reduced pressure
  9. customEvaporate the fractions
  10. additioncontaining the product under reduced pressure
  11. customvacuum oven dry at 40° C.

Sources & evidence

ORD record
ord-01a92994e35b4af5b082468b5d464a20
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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