Hydrochloric Acid → HCID 66653630, compound

HRID 409535Notes

Reaction equation

HRID 409535 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[NH2:20][C:21]1[CH:30]=[CH:29][C:28]([C:31]([C:33]2[N:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:36]3=[C:35](Br)[N:34]=2)=[O:32])=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24].Cl.CI.C(=O)([O-])[O-].[Cs+].[Cs+]>O.COCCOC.CN(C=O)C.CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:20][C:21]1[CH:30]=[CH:29][C:28]([C:31]([C:33]2[N:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:36]3=[C:35]([C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=3)[N:34]=2)=[O:32])=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24]

Participants

12

Reactant 6

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 57500383HCID 57500383, compound

Product 1

HCID 66653630HCID 66653630, compoundYield 76.7%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

0.248 g (1.38 mmol) of [4-(methoxycarbonyl)phenyl]boronic acid, 0.57 g (2.30 mmol) of potassium carbonate in 2 ml of water, and 0.027 g (0.02 mmol) of tetrakis(triphenylphosphine)palladium are added to a solution of 0.43 g (1.15 mmol) of methyl 2-amino-5-[(1-bromoimidazo[1,5-a]pyridin-3-yl)carbonyl]benzoate in 10 ml of DME, under an inert argon atmosphere. The reaction medium is heated at 90° C. for 2 hours. The reaction medium is acidified with a 1N aqueous solution of hydrochloric acid, and extracted with dichloromethane. The organic phase is washed with water, dried over sodium sulphate, filtered, and concentrated under reduced pressure. The solid obtained is dissolved in 5 ml of DMF. 30 μl (0.5 mmol) of methyl iodide and 0.052 g (0.16 mmol) of caesium carbonate are added. After stirring for 24 hours at ambient temperature, the reaction medium is hydrolysed with water and then extracted with ethyl acetate. The organic phase is dried over sodium sulphate, filtered, and then concentrated under reduced pressure. The solid obtained is taken up in methanol. After filtration and drying overnight at 50° C. under reduced pressure, 0.379 g of a yellow powder is obtained.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe solid obtained
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic phase is dried over sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe solid obtained
  12. filtrationAfter filtration
  13. customdrying overnight at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-151d6c5b53f44f44a9fd7e012f901897
Source dataset
uspto-grants-2014_06
Patent number
US08759344B2

Reaction notes

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