3-Bromoquinoline → HCID 18187735, compound

HRID 2303619Notes

Reaction equation

HRID 2303619 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].B1C2CCCC1CCC2.C[O-:27].[Na+].Br[C:30]1[CH:31]=[N:32][C:33]2[C:38]([CH:39]=1)=[CH:37][CH:36]=[CH:35][CH:34]=2>C1COCC1>[C:13]([O-:12])(=[O:27])[CH3:16].[C:13]([O:12][C:10]([N:7]1[CH2:8][CH2:9][CH:4]([CH2:1][CH2:2][CH2:3][C:30]2[CH:31]=[N:32][C:33]3[C:38]([CH:39]=2)=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:5][CH2:6]1)=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 214133-BromoquinolineHCID 789669-Borabicyclo(3.3.1)nonaneHCID 10942334Sodium MethoxideHCID 11117722tert-Butyl 4-(prop-2-en-1-yl)piperidine-1-carboxylate

Product 2

HCID 175AcetateHCID 18187735HCID 18187735, compoundYield 117.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-(t-butoxycarbonyl)-4-(prop-2-en-1-yl)piperidine (from Procedure 5, Step B) (260 mg, 1.15 mmol) in THF (3 mL) under argon was treated with 0.5M 9-BBN solution in THF (2.30 mL, 1.15 mmol). The resulting mixture was stirred at rt for 2 h, then treated with sodium methoxide (68 mg, 1.25 mmol). The resulting mixture was stirred until it was homogeneous (˜15 min) and then was treated with 3-(bromo) quinoline (0.155 mL, 1.15 mmol) and [1,1′-bis(triphenylphosphino)ferrocene)dichloropalladium methylene chloride (41 mg, 0.05 mmol). The resulting mixture was heated at reflux for 30 min, cooled and quenched with 1N NaOH (20 mL). The quenched reaction was extracted with 2×50 mL of ether; the extracts were dried over magnesium sulfate, combined and concentrated. FC (15 g of silica gel, 4:1 v/v hexaneslethyl acetate) afforded the title compound (240 mg).

Workup

  1. stirringThe resulting mixture was stirred until it
  2. custom(˜15 min)
  3. temperatureThe resulting mixture was heated
  4. temperatureat reflux for 30 min
  5. temperaturecooled
  6. customquenched with 1N NaOH (20 mL)
  7. customThe quenched reaction
  8. extractionwas extracted with 2×50 mL of ether
  9. dry with materialthe extracts were dried over magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-437051f11a0e4d8b981845da134cc784
Source dataset
uspto-grants-2002_08
Patent number
US06432981B1

Reaction notes

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