Triphenylphosphine → 6-(1-Isopropyl-pyrrolidin-3-yloxy)-quinoline-2-carboxylic acid ethyl ester

HRID 493426Notes

Reaction equation

HRID 493426 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:16])[CH:12]=2)[N:7]=1)=[O:5])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:36]([N:39]1[CH2:43][CH2:42][CH:41](O)[CH2:40]1)([CH3:38])[CH3:37]>C1(C)C=CC=CC=1.C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH:41]3[CH2:42][CH2:43][N:39]([CH:36]([CH3:38])[CH3:37])[CH2:40]3)[CH:12]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 113095221-Isopropyl-3-pyrrolidinolHCID 57681568Ethyl 6-hydroxyquinoline-2-carboxylate

Product 1

HCID 576815776-(1-Isopropyl-pyrrolidin-3-yloxy)-quinoline-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 0.960 g (0.0044 mol) of 6-hydroxy-quinoline-2-carboxylic acid ethyl ester, 2.32 g (0.0088 mmol) of triphenylphospine (Fluka), 0.739 g (0.0057 mmol) of 1-isopropyl-3-pyrrolidinol and 1.61 ml (0.0088 mmol) of di-tert.-butyl azadicarboxylate 40% in toluene in 100 ml THF was stirred for a prolonged period of time at 35° C. The mixture was filtered through a pad of silica and washed with 30 ml of THF. The mixture was evaporated to dryness and purified on silica eluting with a gradient of DCM/MeOH 98/2. The product fractions were evaporated and the residue was triturated with diethyl ether to yield after drying under vacuum 1.35 g (94%) of the title compound as white solid. MS (m/e): 329.3 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a pad of silica
  2. washwashed with 30 ml of THF
  3. customThe mixture was evaporated to dryness
  4. custompurified on silica eluting with a gradient of DCM/MeOH 98/2
  5. customThe product fractions were evaporated
  6. customthe residue was triturated with diethyl ether
  7. customto yield
  8. dry with materialafter drying under vacuum 1.35 g (94%) of the title compound as white solid

Sources & evidence

ORD record
ord-a68c0a7d713c4a938be341a916686632
Source dataset
uspto-grants-2009_05
Patent number
US07534891B2

Reaction notes

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