Potassium Phosphate, Tribasic → HCID 57863434, compound

HRID 1446737Notes

Reaction equation

HRID 1446737 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:31]=[CH:30][C:14]([CH2:15][NH:16][C:17]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=4)=[O:18])=[CH:13][CH:12]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1.[CH3:32][O:33][C:34]1[N:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].O.C(Cl)Cl.O1CCOCC1.O>[CH3:32][O:33][C:34]1[N:39]=[CH:38][C:37]([C:2]2[CH:7]=[CH:6][N:5]3[C:8]([C:11]4[CH:31]=[CH:30][C:14]([CH2:15][NH:16][C:17]([NH:19][C:20]5[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=5)=[O:18])=[CH:13][CH:12]=4)=[CH:9][N:10]=[C:4]3[CH:3]=2)=[CH:36][CH:35]=1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 685391571-[4-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-benzyl]-3-(3-trifluoromethyl-phenyl)-urea

Product 1

HCID 57863434HCID 57863434, compoundYield 56%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
40 °C

Procedure

Load a 5 mL septum capped vial with the following: small magnetic stir bar, 1-[4-(7-chloro-imidazo[1,2-a]pyridin-3-yl)-benzyl]-3-(3-trifluoromethyl-phenyl)-urea (208 mg, 0.46 mmol), 6-methoxy-pyridin-3-yl boronic acid (0.51 mmols, 1.1 Eq), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (23.6 mg), Pd(OAc)2 (5 mg), K3PO4 (218 mg, 1.03 mmol), dioxane:H2O 2:1 (3 mL). Deoxygenate the reaction with N2 and heat to 40° C. for 24 hours. Cool the mixture and pour into a separatory funnel containing CH2Cl2 (45 mL) and H2O (2 mL). Extract the CH2Cl2 and evaporate under reduced pressure. Mix the residue with CH2Cl2 and a small amount of acetone. Filter the resulting solid and rinse with a small amount of CH2Cl2 and air dry. Vacuum oven dry the solid at 40° C. to give the title compound in 56% yield: MS(ES), m/z 518 (M+1).

Workup

  1. customDeoxygenate
  2. customthe reaction with N2
  3. temperatureCool the mixture
  4. additionpour into a separatory funnel
  5. extractionExtract the CH2Cl2
  6. customevaporate under reduced pressure
  7. additionMix the residue with CH2Cl2
  8. filtrationFilter the resulting solid
  9. washrinse with a small amount of CH2Cl2 and air
  10. customdry
  11. customVacuum oven dry the solid at 40° C.

Sources & evidence

ORD record
ord-e0fa3a5d91f84fd294873502d8f2062f
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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