Nitrogen → 1-(Benzyloxy)-7-methoxy-3-(pyridin-3-yl)isoquinoline

HRID 1520347Notes

Reaction equation

HRID 1520347 reaction equation
N#N.[CH2:3]([O:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=2)[CH:14]=[C:13](Cl)[N:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:3]([O:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=2)[CH:14]=[C:13]([C:20]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[N:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 866770731-(Benzyloxy)-3-chloro-7-methoxyisoquinoline

Product 1

HCID 672980221-(Benzyloxy)-7-methoxy-3-(pyridin-3-yl)isoquinoline

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

1-(Benzyloxy)-7-methoxy-3-(pyridin-3-yl)isoquinoline was prepared using Method N2. 1-(Benzyloxy)-3-chloro-7-methoxyisoquinoline (93 mg, 0.5 mmol, 1.0 eq.), potassium carbonate (357 mg, 2.5 mmol, 5.0 eq.), and Pd(PPh3)2Cl2 (18 mg, 0.026 mmol, 0.05 eq.) was dissolved in the mixed solvent of 1,4-dioxane (3 mL) and water (1 mL). The resulting mixture was stirred at 120° C. for 30 min under the microwave condition. The solid was filtrated off and the filtrate was concentrated. The residue was partitioned between ethyl acetate and water. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate. After filtration and evaporation, the residue was purified by silica gel chromatography (petroleum ether/ethyl acetate=1:10) to afford 100 mg of xxxviii-a as a yellow solid (84.7%).

Workup

  1. filtrationThe solid was filtrated off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration and evaporation
  7. customthe residue was purified by silica gel chromatography (petroleum ether/ethyl acetate=1:10)

Sources & evidence

ORD record
ord-887030c17af640a891c6bf8801b8fd64
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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