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Sodium hydride → 4-Bromo-2-(((2-(5,5-dimethyl-1-cyclopenten-1-yl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)pyridine

HRID 1662574
Notes
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Reaction equation

HRID 1662574 reaction equation
[CH3:1][C:2]1([CH3:24])[C:6]([C:7]2[CH:12]=[C:11]([CH2:13][OH:14])[CH:10]=[CH:9][C:8]=2[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=2[F:23])=[CH:5][CH2:4][CH2:3]1.[H-].[Na+].[Br:27][C:28]1[CH:33]=[CH:32][N:31]=[C:30](F)[CH:29]=1>CN(C=O)C.O>[Br:27][C:28]1[CH:33]=[CH:32][N:31]=[C:30]([O:14][CH2:13][C:11]2[CH:10]=[CH:9][C:8]([C:15]3[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=3[F:23])=[C:7]([C:6]3[C:2]([CH3:24])([CH3:1])[CH2:3][CH2:4][CH:5]=3)[CH:12]=2)[CH:29]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27628514-Bromo-2-fluoropyridineHCID 57705550(2-(5,5-Dimethyl-1-cyclopenten-1-yl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methanol

Product 1

HCID 577058284-Bromo-2-(((2-(5,5-dimethyl-1-cyclopenten-1-yl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)pyridineYield 76%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A dry round bottom flask containing 14.3 (0.0937 g, 0.287 mmol) in dry DMF (1 mL) was cooled in an ice bath. After 10 minutes, sodium hydride (60% wt. in oil) (15.4 mg, 0.385 mmol) was added carefully, and the mixture was stirred at 0° C. After 10 minutes, 4-bromo-2-fluoropyridine (commercially available from Synthonix Corporation) (0.0511 g, 0.290 mmol) was added. The reaction was allowed to stir overnight at room temperature. After 18 hours, the reaction was diluted with water and extracted five times with EtOAc. The combined organic layers were then washed one time with brine and dried over anhydrous magnesium sulfate. The solid was filtered off, and the solvent was concentrated. The residue was purified by silica gel flash chromatography (0-45% EtOAc/hexane) to afford 95.A (105.9 mg, 76% yield). 1H NMR (400 MHz) (CDCl3) δ ppm 8.02 (1H, d, J=4.7 Hz), 7.41 (1H, m), 7.35 (2H, m), 7.08 (2H, m), 7.00 (1H, m), 6.79 (2H, dt, J=5.1, 2.5 Hz), 5.52 (1H, s), 5.42 (2H, s), 3.76 (3H, s), 2.25 (2H, td, J=6.9, 2.5 Hz), 1.67 (2H, t, J=7.0 Hz), 0.87 (6H, s).

Workup

  1. temperaturewas cooled in an ice bath
  2. waitAfter 10 minutes
  3. stirringto stir overnight at room temperature
  4. waitAfter 18 hours
  5. extractionextracted five times with EtOAc
  6. washThe combined organic layers were then washed one time with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe solid was filtered off
  9. concentrationthe solvent was concentrated
  10. customThe residue was purified by silica gel flash chromatography (0-45% EtOAc/hexane)

Sources & evidence

ORD record
ord-07442478960f4e04b91bd07c4dc7aa98
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08030354B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes