Sodium Carbonate → HCID 20814970, compound

HRID 896655Notes

Reaction equation

HRID 896655 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=1.Br[C:22]1[CH:23]=[C:24]([CH:32]([CH3:34])[CH3:33])[CH:25]=[C:26]2[C:31]=1[N:30]=[CH:29][CH:28]=[CH:27]2.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.O.C(OCC)(=O)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>[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:22]2[CH:23]=[C:24]([CH:32]([CH3:34])[CH3:33])[CH:25]=[C:26]3[C:31]=2[N:30]=[CH:29][CH:28]=[CH:27]3)[CH:6]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 110977913-(2-Methoxy-2-oxoethyl)phenylboronic acid, pinacol esterHCID 218655558-Bromo-6-(propan-2-yl)quinoline

Product 1

HCID 20814970HCID 20814970, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
21 °C

Procedure

A solution of [3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester from Step 2 (4 g, 14 mmol), 8-bromo-6-isopropylquinoline (3 g, 12 mmol), Na2CO3 (2M, 18 mL, 36 mmol) and Pd(PPh3)4 (692 mg, 0.6 mmol) in DMF (250 mL) was heated at 80° C. under N2 for 18 h. The resulting reaction mixture was cooled to 21° C. and diluted with water and ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 80:20) provided the [3-(6-Isopropyl-quinolin-8-yl)-phenyl]-acetic acid methyl ester compound.

Workup

  1. customThe resulting reaction mixture
  2. washThe organic extracts were washed (H2O, brine)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. washby flash chromatography (eluting with hexane/ethyl acetate, 80:20)

Sources & evidence

ORD record
ord-5b287d9b692446beb1cf3e469962ecf2
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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