3-Bromoquinoline → (5-Oxo-5-quinolin-3-yl-pentyl)-carbamic acid tert-butyl ester

HRID 1004281Notes

Reaction equation

HRID 1004281 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Li]CCCC.[C:17]([O:21][C:22](=[O:34])[NH:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](=[O:33])N(OC)C)([CH3:20])([CH3:19])[CH3:18]>C(OCC)C>[C:17]([O:21][C:22](=[O:34])[NH:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](=[O:33])[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 214133-BromoquinolineHCID 17958956Tert-butyl (5-(methoxy(methyl)amino)-5-oxopentyl)carbamateHCID 178418339Butyllithium

Product 1

HCID 53998977(5-Oxo-5-quinolin-3-yl-pentyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 3-bromoquinoline (25 g, 120 mmol) in diethyl ether -78° C. was added nBuLi (2.5M THF, 48 ml, 120 mmol) dropwise over 30 minutes. After 30 minutes, 21-2 (3.9 g, 15 mmol), dissolved in 50 ml ether was added dropwise over 10 minutes. After 30 minutes, the cooling bath was removed. After 1.0 hour, the reaction was quenched with sat. NH4Cl. The organic portion was separated, washed with brine, dried (MgSO4) and concentrated. The residue was chromatographed (silica gel, 20-50% ethyl acetate/hexanes) to give 21-3 as a yellow solid.

Workup

  1. additionwas added dropwise over 10 minutes
  2. waitAfter 30 minutes
  3. customthe cooling bath was removed
  4. waitAfter 1.0 hour
  5. customthe reaction was quenched with sat. NH4Cl
  6. customThe organic portion was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue was chromatographed (silica gel, 20-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b0faace947854ecd975c77be4d247879
Source dataset
uspto-grants-2000_04
Patent number
US06048861

Reaction notes

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