Potassium Carbonate → HCID 89499550, compound

HRID 333672Notes

Reaction equation

HRID 333672 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([O:14][CH3:15])=[N:4][C:3]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.[CH3:24][Si:25]([C:28]#[C:29][B-](F)(F)F)([CH3:27])[CH3:26].[K+].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C>[CH3:15][O:14][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=2)[C:2]([C:29]#[C:28][Si:25]([CH3:27])([CH3:26])[CH3:24])=[C:3]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:4]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 23673582PotassiuM (2-triMethylsilyl)ethynyltrifluoroborateHCID 53379588HCID 53379588, compound2×

Product 1

HCID 89499550HCID 89499550, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenylCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the compound 4-bromo-1,7-dimethoxy-3-(4-methoxyphenyl)isoquinoline (compound 26) (187 mg, 0.5 mmol), potassium (trimethylsilyl)ethynyltrifluoroborate (133 mg, 0.65 mmol), palladium diacetate (3.5 mg, 0.015 mmol), RuPhos (14 mg, 0.03 mmol) and potassium carbonate (318 mg, 1.5 mmol) dissolved in 2 mL of a distilled THF/degassed H2O mixture (10/1) is refluxed under argon for 2 hours. The reaction medium is filtered on silica then condensed under vacuum. The crude is purified on a silica column (cyclohexane/dichloromethane, 7/3). 182 mg (93%) of the 1,7-dimethoxy-3-(4-methoxyphenyl)-4-((trimethylsilyl)ethynyl)isoquinoline intermediate is obtained in the form of a brown solid which is used directly in the following stage,

Workup

  1. customdegassed H2O mixture (10/1)
  2. temperatureis refluxed under argon for 2 hours
  3. filtrationThe reaction medium is filtered on silica
  4. customcondensed under vacuum
  5. customThe crude is purified on a silica column (cyclohexane/dichloromethane, 7/3)

Sources & evidence

ORD record
ord-564cf0f97e8542a087471acfd4caaa68
Source dataset
uspto-grants-2014_11
Patent number
US08883763B2

Reaction notes

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