3-Chloromethyl-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine → {2-Methyl-4-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethoxy]-phenylsulfanyl}-acetic acid tert-butyl ester

HRID 1242509Notes

Reaction equation

HRID 1242509 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7][S:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH3:16])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:19][C:20]1[C:21]([CH3:36])=[N:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)=[CH:24][CH:25]=1>>[C:1]([O:5][C:6](=[O:17])[CH2:7][S:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:19][C:20]2[C:21]([CH3:36])=[N:22][C:23]([C:26]3[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:31]=3)=[CH:24][CH:25]=2)=[CH:11][C:10]=1[CH3:16])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 219357513-Chloromethyl-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridineHCID 67072245(4-Hydroxy-2-methyl-phenylsulfanyl)-acetic acid tert-butyl ester

Product 1

HCID 67072399{2-Methyl-4-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethoxy]-phenylsulfanyl}-acetic acid tert-butyl ester

Procedure

In analogy to the procedure described in example 20A], (4-hydroxy-2-methyl-phenylsulfanyl)-acetic acid tert-butyl ester (example 20C]), was reacted with 3-chloromethyl-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine (example 1N]) to give {2-methyl-4-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethoxy]-phenylsulfanyl}-acetic acid tert-butyl ester, which was subsequently saponified in analogy to the procedure described in example 20B] to yield the title compound as white solid of mp. 168–169° C.

Sources & evidence

ORD record
ord-76d191a87f2b4ba6960fade82f3019c2
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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