3-Bromoquinoline → HCID 18187735, compound

HRID 1386711Notes

Reaction equation

HRID 1386711 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]=[CH2:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B1C2CCCC1CCC2.C[O-].[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(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][C:30]2[CH:31]=[N:32][C:33]3[C:38]([CH:39]=2)=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

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 1

HCID 18187735HCID 18187735, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 260 mg (1.15 mmol) of 1-(t-butoxycarbonyl)-4-(prop-2-enyl)piperidine (from EXAMPLE 33, Step B) in 3 mL of THF under argon was treated with 2.30 mL of 0.5 M 9-BBN solution in THF. The resulting mixture was stirred at rt for 2 h, then treated with 68 mg (1.25 mmol) of NaOMe. The resulting mixture was stirred until it was homogeneous (˜15 min) and then was treated with 0.155 mL (1.15 mmol) of 3-(bromo)quinoline and 41 mg (0.05 mmol) of [1,1′-bis(triphenyl-phosphino)ferrocene]dichloropalladium.CH2Cl2. The resulting mixture was heated at reflux for 30 min, cooled and quenched with 20 mL of 1.0 N NaOH. The quenched reaction was extracted with 2×50 mL of ether; the extracts were dried over MgSO4, combined and concentrated. Flash chromatography on 15 g of silica gel using 4:1 v/v hexanes/EtOAc as the eluant afforded 240 mg (59%) of the title compound: 1H NMR (300 MHz) B 1.00-1.16 (m, 2H), 1.25-1.40 (m, 2H), 1.45 (s, 9H), 1.60-1.80 (5H), 2.62-2.72 (m, 2H), 2.79 (t, J=7.8,22H), 4.06 (br s, 2H), 7.52 (m, 1H), 7.66 (m, 1H), 7.76 (dd, J=8.0, 1.6, 1H), 7.91 (d, J=1.6, 1H), 8.77 (d, J=2.2, 1H).

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 20 mL of 1.0 N NaOH
  7. customThe quenched reaction
  8. extractionwas extracted with 2×50 mL of ether
  9. dry with materialthe extracts were dried over MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-46a2a39942cb4a1a87160475ba05e6d5
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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