Potassium Carbonate → Ethyl 3-benzyl-2,4-dimethylquinoline-6-carboxylate

HRID 928765Notes

Reaction equation

HRID 928765 reaction equation
C([C:8]1[C:9](Br)=[N:10][C:11]2[C:16](C=1Br)=[CH:15][C:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=2)C1C=CC=CC=1.CB1OB(C)OB(C)O1.C([O-])([O-])=O.[K+].[K+].O1CCO[CH2:42][CH2:41]1.[CH3:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52].[CH3:53]COC(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>[CH2:48]([C:47]1[C:9]([CH3:8])=[N:10][C:11]2[C:16]([C:46]=1[CH3:53])=[CH:15][C:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=2)[C:49]1[CH:42]=[CH:41][CH:52]=[CH:51][CH:50]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 574072TrimethylboroxineHCID 21899848Ethylacetate heptaneHCID 86715608Ethyl 3-benzyl-2,4-dibromoquinoline-6-carboxylate

Product 1

HCID 86715607Ethyl 3-benzyl-2,4-dimethylquinoline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of ethyl 3-benzyl-2,4-dibromoquinoline-6-carboxylate (0.245 g, 0.545 mmol, Intermediate 34: step a), 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (0.229 mL, 1.64 mmol), and 5 M aqueous K2CO3 (0.436 mL, 2.18 mmol) was treated with Pd(PPh3)4 (63 mg, 0.055 mmol) and dioxane (3 mL). This was microwaved under argon at 140° C. for 15 minutes (Biotage Initiator). The reaction was diluted with 1:1 heptane/EtOAc (5 mL), filtered, and the organic layer was dried (Na2SO4), filtered, and concentrated. The residue was flash chromatographed with a heptane to 70% EtOAc/heptane gradient to provide the title compound as a clear amber oil that crystallized upon standing.

Workup

  1. customThis was microwaved under argon at 140° C. for 15 minutes (Biotage Initiator)
  2. filtrationfiltered
  3. dry with materialthe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed with a heptane to 70% EtOAc/heptane gradient

Sources & evidence

ORD record
ord-c9438e521f0d404d8d6fdf3c43217bb7
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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