Sodium Hydroxide → N-(6-Bromothiazolo[5,4-b]pyridin-2-yl)benzamide

HRID 2068711Notes

Reaction equation

HRID 2068711 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[S:11])[C:5](F)=[N:6][CH:7]=1.[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[N:9]=[C:10]([NH:12][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[S:11][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59603087HCID 59603087, compound

Product 1

HCID 11002134N-(6-Bromothiazolo[5,4-b]pyridin-2-yl)benzamideYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To an ice-cold solution of N-(5-bromo-2-fluoropyridin-3-ylcarbamothioyl)benzamide II (1.80 g, 5.08 mmol) in THF (20.0 mL) was added a solution of NaOH (1.0 g, 22.0 mmol, dissolved in 10.0 mL H2O). The reaction mixture was then heated to 60° C. for 16 h. After the completion of the reaction (TLC monitoring), the reaction mixture was concentrated, added water 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 (1.60 g, 95%). 1H NMR (400 MHz, DMSO-d6): δ 7.42 (m, 3H), 7.82 (d, J=2.0 Hz, 1H), 8.14 (m, 2H) and 8.18 (d, J=2.0 Hz, 1H).

Workup

  1. customAfter the completion of the reaction (TLC monitoring)
  2. concentrationthe reaction mixture was concentrated
  3. additionadded water
  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-f1ea4c5daa35455ca5d3bdd4882dd3bd
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

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