Sodium Hydroxide → 6-Bromo[1,3]thiazolo[5,4-b]pyridin-2-amine

HRID 2068712Notes

Reaction equation

HRID 2068712 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([NH:11]C(=O)C3C=CC=CC=3)[S:8][C:5]2=[N:6][CH:7]=1.[OH-].[Na+]>OS(O)(=O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([NH2:11])[S:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11002134N-(6-Bromothiazolo[5,4-b]pyridin-2-yl)benzamide

Product 1

HCID 446127746-Bromo[1,3]thiazolo[5,4-b]pyridin-2-amineYield 98%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of N-(6-bromothiazolo[5,4-b]pyridin-2-yl)benzamide III (2.0 g, 5.98 mmol) in 70% H2SO4 (10.0 mL) was heated to 140° C. for 1 h. After the completion of the reaction (TLC monitoring), the reaction mixture was poured onto crushed ice, basified with 30% aqueous NaOH solution till pH 8.0 and extracted with EtOAc (3×150 mL). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to obtain the desired product (1.34 g, 98%). 1H NMR (400 MHz, DMSO-d6): δ 7.85 (d, J=2.0 Hz, 1H), 8.05 (br s, 2H) and 8.18 (d, J=2.0 Hz, 1H).

Workup

  1. customAfter the completion of the reaction (TLC monitoring)
  2. additionthe reaction mixture was poured
  3. customonto crushed ice
  4. extractionextracted with EtOAc (3×150 mL)
  5. washThe combined organics was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-17fc1aa22e424997bb1c4c379aafca86
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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