Aluminium lithium hydride → 3-(4-[[3-(4-Chlorophenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]-3,5-difluorophenyl)-2-methylpropan-1-ol

HRID 2177253Notes

Reaction equation

HRID 2177253 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:18]([CH2:19][O:20][C:21]3[C:26]([F:27])=[CH:25][C:24]([CH2:28][CH:29]([CH3:35])[C:30](OCC)=[O:31])=[CH:23][C:22]=3[F:36])=[C:17]([C:37]([F:40])([F:39])[F:38])[S:16][N:15]=2)=[CH:10][CH:9]=1>>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:18]([CH2:19][O:20][C:21]3[C:26]([F:27])=[CH:25][C:24]([CH2:28][CH:29]([CH3:35])[CH2:30][OH:31])=[CH:23][C:22]=3[F:36])=[C:17]([C:37]([F:39])([F:40])[F:38])[S:16][N:15]=2)=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90418793Ethyl 3-(4-((3-(4-chlorophenyl)-5-(trifluoromethyl)isothiazol-4-yl)methoxy)-3,5-difluorophenyl)-2-methylpropanoate

Product 1

HCID 904186933-(4-[[3-(4-Chlorophenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]-3,5-difluorophenyl)-2-methylpropan-1-ol

Procedure

The title compound was prepared according to the procedure described in Example 111 by LAH reduction of ethyl 3-(4-((3-(4-chlorophenyl)-5-(trifluoromethyl)isothiazol-4-yl)methoxy)-3,5-difluorophenyl)-2-methylpropanoate to afford the desired product as an off-white solid. 1H NMR (CDCl3): 7.82 (d, J=7.2 Hz, 2H), 7.52 (d, J=7.2 Hz, 2H), 6.79-6.85 (m, 2H), 5.20 (s, 2H), 3.33-3.41 (m, 2H), 2.76 (dd, J1=5.2 Hz, J2=5.2 Hz, 1H), 2.74-2.79 (m, 1H), 1.82-1.91 (m, 1H), 0.89 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C21H17ClF5NO2S, 478.1 (M+H). found 478.1.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-47600f7adebe4c42b12683ed3442c696
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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