Sodium Carbonate → HCID 57584945, compound

HRID 2077499Notes

Reaction equation

HRID 2077499 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[N:3]=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.CS(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([S:8]([C:4]2[N: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]=[CH:6][CH:5]=2)(=[O:10])=[O:9])=[CH:12][CH:13]=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 57585027HCID 57585027, compound

Product 1

HCID 57584945HCID 57584945, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 679Dimethyl SulfoxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

2-Chloro-6-(4-methoxyphenylsulfonyl)pyridine (0.300 g, 1.06 mmol) was dissolved in 1,4-dioxane (6 mL) and then N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (0.4 g, 1 mmol), tetrakis(triphenylphosphine)palladium (0) (0.2 g, 0.1 mmol) and 2M sodium carbonate (1 mL, 2 mmol) were added to it. The flask was fit with a reflux condensor and placed into a pre-heated (95° C.) bath. The mixture was allowed to stir under inert atmosphere overnight. The mixture was allowed to cool to ambient temperature and diluted with DMSO. The crude was filtered and purified by reverse-phase HPLC. This gave N-(6-(6-(4-methoxyphenylsulfonyl)pyridin-2-yl)benzo[d]thiazol-2-yl)acetamide as an off-white solid. MS (ESI pos. ion) m/z: 440 (MH+). Calculated exact mass for C21H17N3O4S2: 439. 1H NMR (400 MHz, DMSO-d6): 8.53 (s, 1H), 8.15-8.24 (m, 2H), 8.02 (br s, 4H), 7.70 (d, J=7.53 Hz, 1H), 7.7.19 (d, J=7.53 Hz, 2H), 3.83 (s, 3H), 2.15 (s, 3H).

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationThe crude was filtered
  3. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-d3c97ccec0414bec91a0df02c93065ac
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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