Hydrochloric Acid → HCID 178479727, compound

HRID 2214744Notes

Reaction equation

HRID 2214744 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:17]([NH:18][C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])=[N:16][NH:15][C:12]3=[N:13][CH:14]=2)O1.Br[C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1.C([O-])(=O)C.[K+].[ClH:37]>CN(C=O)C.CCO.O.CCOC(C)=O.C(OCC)C.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>[ClH:37].[N:28]1[CH:29]=[CH:30][CH:31]=[C:26]([C:9]2[CH:10]=[C:11]3[C:17]([NH:18][C:19]([CH:21]4[CH2:22][CH2:23]4)=[O:20])=[N:16][NH:15][C:12]3=[N:13][CH:14]=2)[CH:27]=1

Participants

11

Reactant 4

HCID 313Hydrochloric AcidHCID 122863-BromopyridineHCID 517044Potassium AcetateHCID 178431099HCID 178431099, compound

Product 1

HCID 178479727HCID 178479727, compound

Reagents, catalysts & solvents 6

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.02 mmol) was added to a stirred and degassed solution of cyclopropanecarboxylic acid [5-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]amide (Description 7; 200 mg, 0.61 mmol), 3-bromopyridine (193 mg, 1.22 mmol) and potassium acetate (179 mg, 1.83 mmol) in DMF (2 mL), EtOH (1 mL) and H2O (1 mL) and the reaction mixture was stirred at 100° C. for 18 h. The reaction mixture was dissolved in EtOAc (100 mL) and washed with saturated aqueous sodium bicarbonate solution (100 mL) and brine (100 mL). The organic extracts were dried (magnesium sulfate) and concentrated. The crude residue was triturated with dichloromethane and a white solid was obtained. This solid was treated with hydrogen chloride (g) in diethyl ether to afford the corresponding salt as a powder.

Workup

  1. stirringthe reaction mixture was stirred at 100° C. for 18 h
  2. washwashed with saturated aqueous sodium bicarbonate solution (100 mL) and brine (100 mL)
  3. dry with materialThe organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated
  5. customThe crude residue was triturated with dichloromethane
  6. customa white solid was obtained

Sources & evidence

ORD record
ord-d7478b92319044d78aabc18cbb3feb4b
Source dataset
uspto-grants-2006_09
Patent number
US07109199B2

Reaction notes

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