Sodium hydride → 2-(Tricyclo[3.3.1.13,7]dec-1-ylmethoxy)-4-iodo-3-methyl-pyridine

HRID 588665Notes

Reaction equation

HRID 588665 reaction equation
[OH:1][CH2:2][C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[H-].[Na+].F[C:16]1[C:21]([CH3:22])=[C:20]([I:23])[CH:19]=[CH:18][N:17]=1>O1CCCC1>[C:3]12([CH2:2][O:1][C:16]3[C:21]([CH3:22])=[C:20]([I:23])[CH:19]=[CH:18][N:17]=3)[CH2:12][CH:7]3[CH2:6][CH:5]([CH2:11][CH:9]([CH2:8]3)[CH2:10]1)[CH2:4]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 117762982-Fluoro-4-iodo-3-methylpyridine

Product 1

HCID 866812622-(Tricyclo[3.3.1.13,7]dec-1-ylmethoxy)-4-iodo-3-methyl-pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-Hydroxylmethyladamantane (249 mg) was dissolved in tetrahydrofuran (3.5 mL) and NaH (24 mg) was added. After the gas evolution ceased, 2-fluoro-4-iodo-3-methylpyridine (237 mg) in tetrahydrofuran (1.5 mL) was added. The reaction mixture was stirred at room temperature for 0.5 hours, quenched with H2O and extracted with ethyl acetate. The combined organic layers were washed with brine and concentrated. The residue was purified by preparative TLC, eluting with petroleum ether to provide the title compound.

Workup

  1. customquenched with H2O
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC
  6. washeluting with petroleum ether

Sources & evidence

ORD record
ord-534ef0dfff344de1b2091e266158e900
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Reaction notes

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