3-(Methylthio)-1-propanol → HCID 116095890, compound

HRID 712669Notes

Reaction equation

HRID 712669 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Br:20][C:21]1[CH:22]=[C:23]([OH:27])[CH:24]=[N:25][CH:26]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[CH3:44][S:45][CH2:46][CH2:47][CH2:48]O>C1COCC1>[Br:20][C:21]1[CH:26]=[N:25][CH:24]=[C:23]([O:27][CH2:48][CH2:47][CH2:46][S:45][CH3:44])[CH:22]=1

Participants

6

Reactant 4

HCID 104483-(Methylthio)-1-propanolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 5995293-Bromo-5-hydroxypyridine

Product 1

HCID 116095890HCID 116095890, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of PPh3 (20 g, 76 mmol) in THF (20 mL) is added a solution of 5-bromo-pyridin-3-ol (5.0 g, 29 mmol) in THF (10 mL). Then a solution of di-tert-butyl azodicarboxylate (16 g, 69 mmol) in THF (10 ml) is added. The mixture is stirred at room temperature for 30 min and 3-methylsulfanyl-propan-1-ol (3.3 g, 31 mmol) is added. The mixture is stirred at room temperature for 16 hrs. Then the solid is filtered and the filterate is concentrated. The residue is purified by flash column chromatography to give 4.5 g of 3-bromo-5-(3-methylsulfanyl-propoxy)-pyridine.

Workup

  1. stirringThe mixture is stirred at room temperature for 16 hrs
  2. filtrationThen the solid is filtered
  3. concentrationthe filterate is concentrated
  4. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-e8501182663e4f6bb116eb896f3567fb
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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