Potassium Carbonate → Ethyl 8-(2-methoxyphenyl)quinoline-3-carboxylate

HRID 1011441Notes

Reaction equation

HRID 1011441 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7]2.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.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>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 22674138Ethyl 8-bromoquinoline-3-carboxylate

Product 1

HCID 23159783Ethyl 8-(2-methoxyphenyl)quinoline-3-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

A solution of ethyl 8-bromoquinoline-3-carboxylate (2.01 g, 10 mmol), prepared as described in Patent WO 2001047891, 2-methoxyphenylboronic acid (2.79 g, 10 mmol), Pd(PPh3)4 (5% mol), K2CO3 (5 g) in DMF/water (3/1) is stirred at 50° C. for 12 hours. The reaction mixture is then pored on water (150 mL). The aqueous phase is extracted with ethyl acetate (3×100 mL). The combined organic layers are washed with water (3×200 mL). The organic phase is dried over magnesium sulfate and evaporated under vacuum to afford the title compound.

Workup

  1. extractionThe aqueous phase is extracted with ethyl acetate (3×100 mL)
  2. washThe combined organic layers are washed with water (3×200 mL)
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-3fbaaf046bf6494f8d115f3c3b6eb9bd
Source dataset
uspto-grants-2011_07
Patent number
US07977354B2

Reaction notes

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