Sodium Iodide → HCID 86668046, compound

HRID 538336Notes

Reaction equation

HRID 538336 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([NH:13][C:14](=[O:17])[CH2:15]Cl)([CH2:11][OH:12])[CH2:9][OH:10])[CH:5]=[CH:4][N:3]=1.CC([O-])(C)C.[K+].[Na+].[I-]>CC(O)(C)C>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2([CH2:11][OH:12])[NH:13][C:14](=[O:17])[CH2:15][O:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 23665647Potassium tert-butoxideHCID 86668045HCID 86668045, compound

Product 1

HCID 86668046HCID 86668046, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of N-[1-(2-bromo-pyridin-4-yl)-2-hydroxy-1-hydroxymethyl-ethyl]-2-chloro-acetamide (8.0 g, 2.48 mmol) in t-BuOH (50 ml) was added t-BuOK (5.5 g, 49.6 mmol) and NaI (0.375 g, 2.48 mmol) and heated to 90° C. for 1 h. Reaction mass was concentrated under reduced pressure and diluted the residue with EtOAc. Organic layer was separated and washed with ammonium chloride solution, brine followed by drying over anhy. Na2SO4. The crude product was purified by column chromatography using 5% methanol in DCM to obtain title compound as a pale brown gum. Yield=3.25 g (46%). TLC (ethyl acetate) Rf=0.17; LCMS: RtH8=0.12; [M+1]+=286.7 and 289.

Workup

  1. customReaction mass
  2. concentrationwas concentrated under reduced pressure
  3. additiondiluted the residue with EtOAc
  4. customOrganic layer was separated
  5. washwashed with ammonium chloride solution, brine
  6. customby drying over anhy
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-c088e2ceecd44f319a43e55573e3d4d9
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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