Sodium Iodide → HCID 14836990, compound

HRID 869908Notes

Reaction equation

HRID 869908 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:18][C:19]#[N:20]>>[Br:8][C:5]1[CH:6]=[CH:7][C:2](=[O:1])[N:3]([CH2:18][C:19]#[N:20])[CH:4]=1

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 178515818HCID 178515818, compound

Product 1

HCID 14836990HCID 14836990, compoundYield 67%

Conditions

Temperature
60 °C

Procedure

2-Hydroxy-5-bromopyridine (5.000 g, 28.74 mmol), potassium carbonate (14.30 g, 9.283 mL, 103.5 mmol), and sodium iodide (1.077 g, 7.185 mmol) were suspended in chloroacetonitrile (10.85 g, 9.095 mL, 143.7 mmol). The reaction mixture was heated to 60° C. and stirred for 2 hours. The reaction mixture was allowed to cool to room temperature, filtered, and the filtercake was washed with dichloromethane and ethyl acetate. The filtrate was concentrated and purified on 120 g of silica gel utilizing a gradient of 0-100% ethyl acetate in hexanes over 45 minutes to yield the pure product as a beige solid (4.1 g, 67%). 1H NMR (400.0 MHz, DMSO-d6) δ 8.11 (d, J=2.7 Hz, 1H), 7.63 (dd, J=2.8, 9.8 Hz, 1H), 6.49 (d, J=9.8 Hz, 1H), 4.94 (s, 2H).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. washthe filtercake was washed with dichloromethane and ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. custompurified on 120 g of silica gel utilizing a gradient of 0-100% ethyl acetate in hexanes over 45 minutes

Sources & evidence

ORD record
ord-bb9554f216564644913bb2822ac0b67d
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

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