Sodium hydride → 2-Methyl-5-[4-(4-trifluoromethyl-phenyl)-pyridin-2-yloxy]-benzothiazole

HRID 730319Notes

Reaction equation

HRID 730319 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[CH3:18][C:19]1[S:20][C:21]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][C:22]=2[N:23]=1.[H-].[Na+]>CN(C=O)C.[Cu]I>[CH3:18][C:19]1[S:20][C:21]2[CH:27]=[CH:26][C:25]([O:28][C:2]3[CH:7]=[C:6]([C:8]4[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=4)[CH:5]=[CH:4][N:3]=3)=[CH:24][C:22]=2[N:23]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 6997992-Methyl-1,3-benzothiazol-5-olHCID 288758632-Chloro-4-(4-trifluoromethylphenyl)pyridine

Product 1

HCID 578079612-Methyl-5-[4-(4-trifluoromethyl-phenyl)-pyridin-2-yloxy]-benzothiazole

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

This material was prepared according to the method described in Example 413 using 2-chloro-4-(4-trifluoromethyl-phenyl)-pyridine (Example 410 (c), 0.16 g, 0.6 mmol), 2-methyl-5-benzothiazolol (0.12 g, 0.7 mmol), sodium hydride (38 mg, 1.0 mmol) and copper (I) iodide (12 mg, 0.06 mmol) in DMF (3 mL). Purification on a Biotage 40S column (3:1 hexanes:EtOAc), provided the title compound as a white solid. MS (ESI, pos. ion) m/z: 367 (M+1). Mp: 160.5-163.5° C. Anal. Calcd for C20H13F3N2OS. 0.25 H2O: C, 61.45; H, 3.48; N, 7.17; S, 8.20. Found: C, 61.45; H, 3.39; N, 7.17; S, 8.31.

Workup

  1. customThis material was prepared
  2. customPurification on a Biotage 40S column (3:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-3d1f83fcf3f04a049035d51fc7360d67
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Reaction notes

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