Aluminium lithium hydride → HCID 90418852, compound

HRID 2177250Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[C:20]([CH2:21][O:22][C:23]4[C:28]([F:29])=[CH:27][C:26]([CH2:30][CH2:31][C:32](OCC)=[O:33])=[CH:25][C:24]=4[F:37])=[C:19]([C:38]([F:41])([F:40])[F:39])[S:18][N:17]=3)=[CH:15][C:10]=2[O:9][CH2:8]1>>[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]3[C:20]([CH2:21][O:22][C:23]4[C:28]([F:29])=[CH:27][C:26]([CH2:30][CH2:31][CH2:32][OH:33])=[CH:25][C:24]=4[F:37])=[C:19]([C:38]([F:40])([F:41])[F:39])[S:18][N:17]=3)=[CH:15][C:10]=2[O:9][CH2:8]1

Participants

Reactant 2

HCID 21226445Aluminium lithium hydride

HCID 90418717HCID 90418717, compound

Product 1

HCID 90418852HCID 90418852, compound

Procedure

The title compound was prepared according to the procedure described in Example 111 by LAH reduction of ethyl 3-(4-((3-(benzo[d][1,3]dioxol-5-yl)-5-(trifluoromethyl) isothiazol-4-yl)methoxy)-3,5-difluorophenyl)propanoate to afford the desired product as an off-white solid. 1H NMR (300 MHz, CD3OD) δ 7.28 (d, J=8.1 Hz, 1H), 7.18 (s, 1H), 6.89 (d, J=8.1 Hz, 1H), 6.80 (d, J=9.3 Hz, 2H), 6.03 (s, 2H), 5.20 (s, 2H), 3.52 (t, J=6.3 Hz, 2H), 2.62 (t, J=7.2 Hz, 2H), 1.82-1.76 (m, 2H). Mass spectrum (ESI, m/z): Calcd. for C21H16F5NO4S, 474.1 (M+H). found 474.1.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-85ed813aac584da79a14590efb2d0232
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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