Potassium Hydroxide → HCID 66632518, compound

HRID 2404243Notes

Reaction equation

HRID 2404243 reaction equation
Br[C:2]1[CH:9]=[C:8]([C:10]2[C:22]3[C:21]4[CH:20]=[C:19]([O:23][CH3:24])[C:18]([O:25][CH3:26])=[CH:17][C:16]=4[N:15]=[CH:14][C:13]=3[NH:12][N:11]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[OH-].[K+].[CH:37](B1OC(C)(C)C(C)(C)O1)=[CH2:38]>CN(C)C=O.O.COCCOC>[CH3:26][O:25][C:18]1[C:19]([O:23][CH3:24])=[CH:20][C:21]2[C:22]3[C:10]([C:8]4[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([CH:37]=[CH2:38])[CH:9]=4)=[N:11][NH:12][C:13]=3[CH:14]=[N:15][C:16]=2[CH:17]=1

Participants

8

Reactant 4

HCID 14797Potassium HydroxideHCID 62657Potassium Phosphate, TribasicHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 66632342HCID 66632342, compound

Product 1

HCID 66632518HCID 66632518, compoundYield 52.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
150 °C

Procedure

2-Bromo-4-(7,8-dimethoxy-3H-pyrazolo[3,4-c]quinolin-1-yl)benzonitrile (540 mg, 1.32 mmol) is dissolved in N,N-dimethylformamide (4.0 ml) under an argon protective-gas atmosphere. Tripotassium phosphate (578 mg, 2.64 mmol), KOH (67 mg, 1.19 mmol), 1,2-dimethoxyethane (9.0 ml) and water (50 μl), vinylboronic acid pinacol ester (942 μl, 5.28 mmol) and trans-bis(tricyclohexylphosphine)palladium(II)dichloride (98 mg, 132 μmol) are subsequently added. The suspension obtained is heated at 150° C. (microwave) for 30 min. For work-up, the mixture is extracted with ethyl acetate and semi-saturated sodium chloride solution. The organic phase is dried over Na2SO4, filtered with suction and evaporated to dryness in vacuo. The residue is purified over flash silica gel (solvent gradient cyclohexane/0-80% by vol. of ethyl acetate), giving 4-(7,8-dimethoxy-3H-pyrazolo[3,4-c]-quinolin-1-yl)-2-vinylbenzonitrile (247 mg, 693 μmol) as a solid. MS: 357.2 (M+H+), TLC (HPTLC): Rf=0.47 (ethyl acetate/ethanol 8:1, parts by volume).

Workup

  1. customThe suspension obtained
  2. extractionFor work-up, the mixture is extracted with ethyl acetate and semi-saturated sodium chloride solution
  3. dry with materialThe organic phase is dried over Na2SO4
  4. filtrationfiltered with suction
  5. customevaporated to dryness in vacuo
  6. customThe residue is purified over flash silica gel (solvent gradient cyclohexane/0-80% by vol. of ethyl acetate)

Sources & evidence

ORD record
ord-3de96287abc14ce6a803ffed8b4980ca
Source dataset
uspto-grants-2014_08
Patent number
US08802712B2

Reaction notes

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