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

HRID 336588Notes

Reaction equation

HRID 336588 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-1ff4b3e44251469c9cb96c31867c8b6e
Source dataset
uspto-grants-2014_11
Patent number
US08889675B2

Reaction notes

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