1,4-Dioxane → HCID 51354600, compound

HRID 2077545Notes

Reaction equation

HRID 2077545 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:21]=[CH:20][C:12]3[N:13]=[C:14]([NH:16][C:17](=[O:19])[CH3:18])[S:15][C:11]=3[CH:10]=2)O1.Br[C:24]1[CH:25]=[C:26]([NH:31][S:32]([C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[C:27]([Cl:30])=[N:28][CH:29]=1.O1CCOCC1>C([O-])([O-])=O.[Na+].[Na+].[Pd]>[Cl:30][C:27]1[N:28]=[CH:29][C:24]([C:9]2[CH:21]=[CH:20][C:12]3[N:13]=[C:14]([NH:16][C:17](=[O:19])[CH3:18])[S:15][C:11]=3[CH:10]=2)=[CH:25][C:26]=1[NH:31][S:32]([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)(=[O:33])=[O:34]

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 51354026n-(6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamideHCID 51355175HCID 51355175, compound

Product 1

HCID 51354600HCID 51354600, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (0.18 g, 0.6 mmol), N-(5-bromo-2-chloropyridin-3-yl)-4-methoxybenzenesulfonamide (0.15 g, 0.4 mmol) and Pd FibreCat® in 1 mL of 10% Na2CO3 and 3 mL of dioxane was heated at 100° C. for 12 minutes. The mixture was then filtered and the filtrate was concentrated in vacuo, washed with small amount of EtOAc, and recrystallized in MeOH to give white solid N-(6-(6-chloro-5-(4-methoxyphenylsulfonamido)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (0.08 g, 41% yield). MS (ESI pos. ion) m/z: calc'd for C21H17ClN4O4S2: 488.0. found: 489.0 (MH+). 1H NMR (300 MHz, MeOH) δ ppm 2.29 (s, 3H) 3.85 (s, 3H) 6.97-7.07 (m, 2H) 7.66 (dd, J=8.48, 1.90 Hz, 1H) 7.70-7.78 (m, 2H) 7.81-7.90 (m, 2H) 8.11 (d, J=1.61 Hz, 1H) 8.17 (d, J=2.34 Hz, 1H) 8.44 (d, J=2.34 Hz, 1H).

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. washwashed with small amount of EtOAc
  4. customrecrystallized in MeOH

Sources & evidence

ORD record
ord-4f94cf15e7554ad2918c56b03d7c9c6b
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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