Cesium carbonate → 3-methyl-6-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-1H-indole

HRID 1767986Notes

Reaction equation

[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[NH:4][CH:3]=1.Cl[CH2:13][C:14]1[S:18][C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)=[N:16][C:15]=1[CH3:29].C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:13][C:14]3[S:18][C:17]([C:19]4[CH:20]=[CH:21][C:22]([C:25]([F:28])([F:26])[F:27])=[CH:23][CH:24]=4)=[N:16][C:15]=3[CH3:29])=[CH:8][CH:9]=2)[NH:4][CH:3]=1

Participants

Reactant 3

HCID 10796Cesium carbonate

HCID 27830065-Chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole

HCID 136625956-Hydroxyskatole

Product 1

HCID 236144963-methyl-6-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-1H-indole

Procedure

In analogy to the procedure described in example 27 e], 3-methyl-1H-indol-6-ol was reacted with 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole [PCT Int. Appl. (2002), WO 0292590 A1] in the presence of cesium carbonate to give 3-methyl-6-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-1H-indole as light brown crystals.

Sources & evidence

ORD record: ord-46d5a25735e148c3a3a255a48e1869ed
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235572B2

Reaction notes

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