Sodium Carbonate → HCID 57585103, compound

HRID 2077560Notes

Reaction equation

HRID 2077560 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]([CH3:22])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:31]2[CH:43]=[CH:42][C:34]3[N:35]=[C:36]([NH:38][C:39](=[O:41])[CH3:40])[S:37][C:33]=3[CH:32]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.[Pd]>[CH3:22][N:8]([C:4]1[CH:3]=[C:2]([C:31]2[CH:43]=[CH:42][C:34]3[N:35]=[C:36]([NH:38][C:39](=[O:41])[CH3:40])[S:37][C:33]=3[CH:32]=2)[CH:7]=[N:6][CH:5]=1)[S:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 51354026n-(6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamideHCID 67097612HCID 67097612, compound

Product 1

HCID 57585103HCID 57585103, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a microwave vial equipped with a stir bar was charged with N-(5-bromopyridin-3-yl)-N-methyl-4-(trifluoromethyl)benzenesulfonamide (0.250 g, 0.6 mmol) in 1,4-dioxane (3 ml), was added N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (0.300 g, 0.9 mmol), Pd FibreCat® (0.024 g, 20%) and 2M sodium carbonate (0.8 ml, 2 mmol). The vial was capped and then placed into a CEM Microwave for 15 minutes at 100° C., while 100 watts of energy was supplied via Powermax® (Simultaneous heating while cooling technology). The progress of the reaction was monitored by LC/MS, which showed desired product, N-deacylated material and boronic ester in the mixture. The reaction was stopped at this point, to prevent further de-acylation of product. The mixture was diluted with DCM and saturated sodium bicarbonate solution. The organic layer was collected by extracting with DCM (3×20 ml). Combined organic extracts, dried over sodium sulfate, filtered and concentrated in vacuo. The crude was diluted with ethyl acetate and stirred 10 minutes. The precipitate was collected by filtration and washed with 1:1 ethyl acetate/hexanes. This gave N-(6-(5-(N-methyl-4-(trifluoromethyl)phenylsulfonamido)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (0.160 g, 50% yield) as a tan crystalline solid. MS (ESI pos. ion) m/z: 507 (MH+). Calc'd exact mass for C22H17F3N4O3S2: 506. 1H NMR (400 MHz, DMSO-d6): 2.23 (s, 3H), 3.31 (s, 3H), 7.71 (d, J=7.53 Hz, 1H), 7.81 (d, J=7.03 Hz, 3H), 7.87 (s, 1H), 8.02 (d, J=6.53 Hz, 2H), 8.26 (s, 1H), 8.42 (s, 1H), 8.91 (s, 1H), 12.44 (s, 1H).

Workup

  1. customTo a microwave vial equipped with a stir bar
  2. customThe vial was capped
  3. temperaturewas supplied via Powermax® (Simultaneous heating while cooling technology)

Sources & evidence

ORD record
ord-729ac2ff3e574ddd8a5c7cfd7d989c03
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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