m-Chloroperbenzoic acid → 2-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]-6-fluoro-5-(piperidin-1-yl)-1H-benzimidazole

HRID 1004598Notes

Reaction equation

HRID 1004598 reaction equation
[CH3:1][C:2]1[C:3]([CH2:14][S:15][C:16]2[NH:20][C:19]3[CH:21]=[C:22]([F:31])[C:23]([N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:24][C:18]=3[N:17]=2)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].ClC1C=CC=C(C(OO)=[O:40])C=1.[K+].[Br-]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:3]([CH2:14][S:15]([C:16]2[NH:20][C:19]3[CH:21]=[C:22]([F:31])[C:23]([N:25]4[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]4)=[CH:24][C:18]=3[N:17]=2)=[O:40])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:11])([F:13])[F:12]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 253877Potassium BromideHCID 187927512-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylthio]-6-fluoro-5-(piperidin-1-yl)-1H-benzimidazole

Product 1

HCID 187927482-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]-6-fluoro-5-(piperidin-1-yl)-1H-benzimidazoleYield 78%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound (0.18 g, 78%) was prepared by the above general procedure using 2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylthio]-6-fluoro-5-(piperidin-1-yl)-1H-benzimidazole (0.23 g, 0.5 mmol) (obtained in example 16), m-chloroperbenzoic acid (50%, 0.2 g, 0.6 mmol) and chloroform (20 mL). mp 99-100° C.; IR (KBr) 3413, 1070 cm- 1; 1H NMR (DMSO-d6) δ 1.52 (m, 2H, CH2), 1.70 (m, 4H, (CH2)2), 2.20 (s, 3H, CH3) 3.98 (t,J=4.5 Hz, 4H, N(CH2)2), 4.80 (ABq,J=12.9 Hz, Δv=9.1 Hz, 2H, SOCH2), 4.94 (q,J=8.1 Hz, 2H, OCH2CF3), 7.12 (d,J=5.8 Hz, 1H), 7.18 (d,J=7.8 Hz, 1H), 7.44 (d,J=12.7 Hz, 1H), 8.32 (d,J=5.5 Hz, 1H); Mass (m/z) 454 (M -16).

Sources & evidence

ORD record
ord-b3f4bead7698468d9b3dca9756aac3c5
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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