Hydrochloric Acid → HCID 178445789, compound

HRID 525450Notes

Reaction equation

HRID 525450 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:15][CH2:14]1)[CH:6]=[CH:5]2.C([Li])CCC.CCCCCC.Cl.[C:35](=O)(O)[O-:36].[Na+]>O1CCCC1.CN(C)C=O>[C:19]([C@H:16]1[CH2:17][CH2:18][C@H:13]([O:12][C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([CH:35]=[O:36])[CH:3]=3)[N:8]=2)[CH2:14][CH2:15]1)([CH3:22])([CH3:21])[CH3:20]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 516892Sodium BicarbonateHCID 178418339ButyllithiumHCID 178445721HCID 178445721, compound

Product 1

HCID 178445789HCID 178445789, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 6-Bromo-2-(trans-4-tert-butyl-cyclohexyloxy)-quinoline (1.0933 g, 3.0176 mmol) in Tetrahydrofuran (24 mL) was added 1.6 M of n-Butyllithium in hexane (5.6 mL, 9.0 mmol) at −78° C. and the reaction was stirred for 15 min. N,N-Dimethylformamide (1.2 mL) was added and the reaction was stirred for 30 minutes. 1 M HCl was added and the reaction allowed to warm to RT. Saturated sodium bicarbonate solution was added and the mixture extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride, dried with sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography using hexanes/ethyl acetate (0-50%) as eluent to give product in 603 mg yield (64%). ESI-MS (M+H+): 312.20.

Workup

  1. stirringthe reaction was stirred for 30 minutes
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography
  8. customto give product in 603 mg
  9. customyield (64%)

Sources & evidence

ORD record
ord-733403825da84c99bc554fc9920bd75f
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Reaction notes

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