Sodium Carbonate → HCID 57584981, compound

HRID 2077553Notes

Reaction equation

HRID 2077553 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:27]2[CH:39]=[CH:38][C:30]3[N:31]=[C:32]([NH:34][C:35](=[O:37])[CH3:36])[S:33][C:29]=3[CH:28]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.[Pd]>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([S:9]([NH:8][C:4]2[CH:3]=[C:2]([C:27]3[CH:39]=[CH:38][C:30]4[N:31]=[C:32]([NH:34][C:35](=[O:37])[CH3:36])[S:33][C:29]=4[CH:28]=3)[CH:7]=[N:6][CH:5]=2)(=[O:11])=[O:10])=[CH:13][CH:14]=1

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 57585105N-(5-Bromopyridin-3-yl)-4-methylbenzene-1-sulfonamide

Product 1

HCID 57584981HCID 57584981, 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)-4-methylbenzenesulfonamide (0.180 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 (0.223 g, 0.7 mmol), Pd FibreCat® (Anchored homogeneous catalyst, Johnson Matthey, West Deptford, N.J.) (0.024 g, 20%) and 2M sodium carbonate (0.7 ml, 1 mmol). The vial was capped and then placed into a CEM Microwave for 10 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 purified by reverse-phase HPLC. This gave N-(6-(5-(4-methylphenylsulfonamido)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (0.016 g, 7% yield) as a white crystalline solid. MS (ESI pos. ion) m/z: 439 (MH+). Calc'd exact mass for C21H18N4O3S2: 438. 1H NMR (400 MHz, DMSO-d6): 2.19 (s, 3H), 2.27 (s, 3H), 7.16 (d, 2H), 7.37 (s, 1H), 7.49 (s, 1H), 7.62 (d, 2H), 7.73 (d, 1H), 7.90 (s, 1H), 7.94 (s, 1H), 8.02 (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-50c4d5429ba74aa48dee501f5843bbf6
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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