1,4-Dibromobenzene → HCID 57420154, compound

HRID 1619211Notes

Reaction equation

HRID 1619211 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[Li]CCCC.[N:14]1[CH:19]=[CH:18][CH:17]=[N:16][C:15]=1[N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1>C1COCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:23]2([OH:26])[CH2:22][CH2:21][N:20]([C:15]3[N:16]=[CH:17][CH:18]=[CH:19][N:14]=3)[CH2:25][CH2:24]2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 78041,4-DibromobenzeneHCID 14788561-Pyrimidin-2-yl-piperidin-4-oneHCID 178418339Butyllithium

Product 1

HCID 57420154HCID 57420154, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1,4-dibromobenzene (213.3 mg, 0.904 mmol) in THF (4 ml), was added n-BuLi (2.5 M in hexanes, 0.362 ml, 0.904 mmol) at −78° C. After being stirred for 30 minutes at the same temperature, a solution of 1-pyrimidin-2-yl-piperidin-4-one (80 mg, 0.452 mmol) in THF (3 ml) was added. The mixture was allowed to warm to room temperature and stirred for 1 hour. The reaction was quenched with addition of water (10 ml) and EtOAc (50 ml). The organic layer was washed with brine (5 ml), dried (MgSO4), filtered, and concentrated under reduced pressure to furnish the crude product. This material was purified by column chromatography (40% EtOAc/hexanes) to give 4-(4-Bromo-phenyl)-1-pyrimidin-2-yl-piperidin-4-ol as a colorless oil (140 mg, 93%): 1H NMR (CDCl3, 400 MHz) δ 8.33 (d, J=6.4 Hz, 2H), 7.47 (d, J=12.0 Hz, 2H), 7.41 (d, J=12.0 Hz, 2H), 6.49 (t, J=6.4 Hz, 1H), 4.72 (m, 2H), 3.40 (m, 2H), 2.05 (m, 2H), 1.78 (m, 2H); MS calc'd for C15H17BrN3O [M+H]+: 335; Found: 335.

Workup

  1. stirringstirred for 1 hour
  2. customThe reaction was quenched with addition of water (10 ml) and EtOAc (50 ml)
  3. washThe organic layer was washed with brine (5 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto furnish the crude product
  8. customThis material was purified by column chromatography (40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ef881fcb6d9f492c877325aeac9beb88
Source dataset
uspto-grants-2014_07
Patent number
US08772291B2

Reaction notes

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