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

HRID 2177254Notes

Reaction equation

HRID 2177254 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]([CH2:20][O:21][C:22]3[C:27]([F:28])=[CH:26][C:25]([CH2:29][CH:30]([CH3:36])[C:31](OCC)=[O:32])=[CH:24][C:23]=3[F:37])=[C:18]([C:38]([F:41])([F:40])[F:39])[S:17][N:16]=2)=[CH:11][CH:10]=1)[CH3:8]>>[CH2:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]([CH2:20][O:21][C:22]3[C:27]([F:28])=[CH:26][C:25]([CH2:29][CH:30]([CH3:36])[CH2:31][OH:32])=[CH:24][C:23]=3[F:37])=[C:18]([C:38]([F:39])([F:40])[F:41])[S:17][N:16]=2)=[CH:11][CH:10]=1)[CH3:8]

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90418138Ethyl 3-(4-((3-(4-ethylphenyl)-5-(trifluoromethyl)isothiazol-4-yl)methoxy)-3,5-difluorophenyl)-2-methylpropanoate

Product 1

HCID 904182903-(4-[[3-(4-Ethylphenyl)-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-ethylphenyl)-5-(trifluoromethyl)isothiazol-4-yl)methoxy)-3,5-difluorophenyl)-2-methylpropanoate to afford the desired product as an off-white solid. 1H NMR (400 MHz, CD3OD) δ 7.71 (d, J=8.0 Hz, 2H), 7.35 (d, J=8.0 Hz, 2H), 6.78-6.84 (m, 2H), 5.21 (s, 2H), 3.41 (d, J=6.8 Hz, 2H), 2.71-2.79 (m, 3H), 2.30-2.36 (m, 1H), 1.82-1.91 (m, 1H), 1.30 (t, J=7.6 Hz, 3H), 0.89 (d, J=6.8 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for C23H22F5NO2S, 472.2 (M+H). found 472.2.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-21786c259c6d42d895fc1444b92bb04b
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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