Aluminium lithium hydride → HCID 90418877, compound

HRID 2177286Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[C:12]([CH2:13][O:14][C:15]2[C:20]([F:21])=[CH:19][C:18]([CH2:22][CH2:23][C:24](OCC)=[O:25])=[C:17]([F:29])[C:16]=2[F:30])=[C:11]([C:31]2[CH:36]=[CH:35][C:34]([CH2:37][CH3:38])=[CH:33][CH:32]=2)[S:10][N:9]=1>>[Cl:7][C:8]1[C:12]([CH2:13][O:14][C:15]2[C:20]([F:21])=[CH:19][C:18]([CH2:22][CH2:23][CH2:24][OH:25])=[C:17]([F:29])[C:16]=2[F:30])=[C:11]([C:31]2[CH:32]=[CH:33][C:34]([CH2:37][CH3:38])=[CH:35][CH:36]=2)[S:10][N:9]=1

Participants

Reactant 2

HCID 21226445Aluminium lithium hydride

HCID 90418701HCID 90418701, compound

Product 1

HCID 90418877HCID 90418877, compound

Procedure

The title compound was prepared according to the procedure described in Example 156 following Step 2 by LAH reduction of ethyl 3-(4-((3-chloro-5-(4-ethylphenyl)isothiazol-4-yl)methoxy)-2,3,5-trifluorophenyl)propanoate to afford the desired product as an off-white solid. 1H NMR (400 MHz, CDCl3) 7.65 (d, J=7.5 Hz, 2H), 7.32 (d, J=7.5 Hz, 2H), 6.74 (m, J=5.5 Hz, 1H), 5.10 (s, 2H), 3.72 (t, J=7.0 Hz, 2H), 2.78 (m, J=5.8 Hz, 2H), 1.88 (m, 2H), 1.55 (br, s, 2H), 1.28 (t, J=7.6 Hz, 2H). LCMS (ESI, M/Z) for C21H19ClF3NO2S: 441.1, 443.1.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-7ed94d9115164d1f814f1266b36b5f87
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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