Sodium Carbonate → N-(6-(2-(4-methoxyphenylsulfonyl)thiazol-5-yl)benzo[d]thiazol-2-yl)acetamide

HRID 2077496Notes

Reaction equation

HRID 2077496 reaction equation
Br[C:2]1[S:6][C:5]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)(=[O:9])=[O:8])=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:26]2[CH:38]=[CH:37][C:29]3[N:30]=[C:31]([NH:33][C:34](=[O:36])[CH3:35])[S:32][C:28]=3[CH:27]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([S:7]([C:5]2[S:6][C:2]([C:26]3[CH:38]=[CH:37][C:29]4[N:30]=[C:31]([NH:33][C:34](=[O:36])[CH3:35])[S:32][C:28]=4[CH:27]=3)=[CH:3][N:4]=2)(=[O:9])=[O:8])=[CH:11][CH:12]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 51354026n-(6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamideHCID 575851575-Bromo-2-(4-methoxyphenylsulfonyl)thiazole

Product 1

HCID 25183186N-(6-(2-(4-methoxyphenylsulfonyl)thiazol-5-yl)benzo[d]thiazol-2-yl)acetamide

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromo-2-(4-methoxyphenylsulfonyl)thiazole (134.8 mg, 4.034 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (163.6 mg, 0.5141 mmol), sodium carbonate (0.40 mL, 2.0 M in water, 0.80 mmol), and palladiumtetrakis(triphenyl phosphine) (59.5 mg, 51.5 μmol) were suspended in 1,4-dioxane (3.2 mL) and the reaction mixture was stirred and heated at 80° C. for 1.5 hours. Additional Pd(PPh3)4 (78 mg) was added to the mixture and stirring and heating were continued at 90° C. for another 90 minutes, at which time the reaction was cooled to RT. The organic phase was decanted, and the residual solid was washed with DCM and MeOH and filtered through a Celite® (diatomaceous earth) pad. This pad was washed with DCM and MeOH, and the filtrate was combined with the decanted suspension and concentrated. The solid was treated with Et2O and filtered. Solid washed with Et2O and purified on HPLC (10% to 95% MeCN/water with 0.1% TFA over 40 minutes) to afford N-(6-(2-(4-methoxyphenylsulfonyl)thiazol-5-yl)benzo[d]thiazol-2-yl)acetamide. MS (ESI pos. ion) m/z: 446. Calculated exact mass for C19H15N3O4S3: 445. 1H NMR (400 MHz, DMSO-d6): 12.51 (s, 1H), 8.48 (s, 1H), 8.45 (s, 1H), 7.99 (d, J=9.0 Hz, 2H), 7.81 (m, 2H), 7.22 (d, J=8.5 Hz, 2H), 3.87 (s, 3H), 2.22 (s, 3H).

Workup

  1. stirringstirring
  2. temperatureheating
  3. temperaturethe reaction was cooled to RT
  4. customThe organic phase was decanted
  5. washthe residual solid was washed with DCM and MeOH
  6. filtrationfiltered through a Celite® (diatomaceous earth) pad
  7. washThis pad was washed with DCM and MeOH
  8. concentrationconcentrated
  9. additionThe solid was treated with Et2O
  10. filtrationfiltered
  11. washSolid washed with Et2O
  12. custompurified on HPLC (10% to 95% MeCN/water with 0.1% TFA over 40 minutes)

Sources & evidence

ORD record
ord-ae6a6842a8c24623beab1e3f484ce3be
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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