Water → N-(5-(3-aminophenyl)thiazolo[5,4-b]pyridin-2-yl)acetamide

HRID 2077540Notes

Reaction equation

HRID 2077540 reaction equation
Br[C:2]1[N:7]=[C:6]2[S:8][C:9]([NH:11][C:12](=[O:14])[CH3:13])=[N:10][C:5]2=[CH:4][CH:3]=1.O.[NH2:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1>[NH2:16][C:17]1[CH:22]=[C:21]([C:2]2[N:7]=[C:6]3[S:8][C:9]([NH:11][C:12](=[O:14])[CH3:13])=[N:10][C:5]3=[CH:4][CH:3]=2)[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 143894233-Aminophenylboronic acid monohydrateHCID 56763853N-(5-Bromothiazolo[5,4-b]pyridin-2-yl)acetamide

Product 1

HCID 57584994N-(5-(3-aminophenyl)thiazolo[5,4-b]pyridin-2-yl)acetamideYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
94.5 °C

Procedure

N-(5-bromothiazolo[5,4-b]pyridin-2-yl)acetamide (1.504 g, 5.527 mmol), 3-aminophenylboronic acid monohydrate (1.316 g, 8.493 mmol), Pd(dppf)C12-DCM complex (604.4 mg, 0.7401 mmol), and potassium carbonate (2.292 g, 16.58 mmol) were suspended in 1,4-dioxane (45 ml) and water (15 ml) was added. Argon was bubbled through the solution for about 30 seconds, and then the flask was fit with a reflux condensor and placed in a preheated oil bath (90-99° C.) and stirred under argon for 4 hours. The reaction was cooled to room temperature, filtered, and the solid was washed with DCM and MeOH. The filtrate was concentrated, treated with DCM and MeOH, and filtered. The solid was collected and set aside, and the filtrate was concentrated, treated with Et2O, and filtered. Solid washed with Et2O. This solid was combined with the first batch and dried under high vacuum first at room temperature, and then at ˜50° C. This solid was treated with deionized water and filtered, and the solid was washed with water, collected, and dried under high vacuum in water bath (˜50° C.) to afford N-(5-(3-aminophenyl)thiazolo[5,4-b]pyridin-2-yl)acetamide (1.22 g, 78% yield). MS (ESI pos. ion) m/z: 285. Calculated exact mass for C14H12N4OS 284.

Workup

  1. customArgon was bubbled through the solution for about 30 seconds
  2. customplaced in a preheated oil bath
  3. temperatureThe reaction was cooled to room temperature
  4. filtrationfiltered
  5. washthe solid was washed with DCM and MeOH
  6. concentrationThe filtrate was concentrated
  7. additiontreated with DCM and MeOH
  8. filtrationfiltered
  9. customThe solid was collected
  10. concentrationthe filtrate was concentrated
  11. additiontreated with Et2O
  12. filtrationfiltered
  13. washSolid washed with Et2O
  14. customdried under high vacuum first at room temperature
  15. customat ˜50° C
  16. additionThis solid was treated with deionized water
  17. filtrationfiltered
  18. washthe solid was washed with water
  19. customcollected
  20. dry with materialdried under high vacuum in water bath (˜50° C.)

Sources & evidence

ORD record
ord-ec330e0dab214f65abf44ab705ca2c98
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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