Boron tribromide → 5-Bromo-2-bromomethyl-thiazolo[5,4-b]pyridine

HRID 415650Notes

Reaction equation

HRID 415650 reaction equation
C(O[CH2:9][C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([Br:19])[N:13]=2)C1C=CC=CC=1.B(Br)(Br)[Br:21]>C([O-])(O)=O.[Na+]>[Br:19][C:14]1[N:13]=[C:12]2[S:11][C:10]([CH2:9][Br:21])=[N:18][C:17]2=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 866432762-Benzyloxymethyl-5-bromo-thiazolo[5,4-b]pyridine

Product 1

HCID 866432755-Bromo-2-bromomethyl-thiazolo[5,4-b]pyridineYield 136.1%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-Benzyloxymethyl-5-bromo-thiazolo[5,4-b]pyridine (1.60 g, 4.77 mmol) DCM (15 mL) was cooled to −78° C. followed by addition of BBr3 (2.27 ml, 23.86 mmol). The reaction mixture was stirred at 25° C. for 2 h. After the completion of the reaction mixture (TLC monitoring), solution of NaHCO3 (20 mL) was added at 0° C. and extracted with ethyl acetate (3×50 mL). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated to get the desired product (2.0 g, Crude yield).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organics was washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cfeb28efa7414b6197e9f243bb1339a4
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

Loading…