Water → Methyl 4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)picolinate

HRID 2175209Notes

Reaction equation

HRID 2175209 reaction equation
[CH3:1][C:2]1[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[C:19]2[C:14](=[C:15](B3OC(C)(C)C(C)(C)O3)[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=[O:9].Br[C:35]1[CH:40]=[CH:39][N:38]=[C:37]([C:41]([O:43][CH3:44])=[O:42])[CH:36]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.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][C:2]1[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[C:19]2[C:14](=[C:15]([C:35]3[CH:40]=[CH:39][N:38]=[C:37]([C:41]([O:43][CH3:44])=[O:42])[CH:36]=3)[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12828947Methyl 4-bromopicolinateHCID 709820304-(2,3-dimethylphenoxy)-1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one

Product 1

HCID 70982851Methyl 4-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)picolinateYield 87%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a degassed solution of 4-(2,3-dimethylphenoxy)-1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one (0.020 g, 0.045 mmol), methyl 4-bromopicolinate (0.019 g, 0.089 mmol) and potassium carbonate (0.018 g, 0.134 mmol) in dioxane (0.50 mL)/water (0.20 mL) was added tetrakis(triphenylphosphine)palladium (2.57 mg, 2.225 μmol). Upon completion of addition, the vial was purged with argon, sealed, and stirred at 90° C. for 16 h. After cooling to room temperature, the mixture was extracted with EtOAc. The combined organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude material was purified by flash chromatography (0-100% ethyl acetate:hexanes) to afford the title compound (17.7 mg, 87% yield) as a clear colorless oil. LCMS, [M+H]+=459.1.

Workup

  1. additionUpon completion of addition
  2. customthe vial was purged with argon
  3. customsealed
  4. temperatureAfter cooling to room temperature
  5. extractionthe mixture was extracted with EtOAc
  6. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by flash chromatography (0-100% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-82c2796a3fae4d198ef030cc3e7b8b9f
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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