Ethyl 3-(2,3-difluoro-4-hydroxyphenyl)propanoate → HCID 85472224, compound

HRID 2177263Notes

Reaction equation

HRID 2177263 reaction equation
[Cl:1][C:2]1[C:6]([CH2:7]Cl)=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[S:4][N:3]=1.[OH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])=[C:20]([F:31])[C:19]=1[F:32]>>[Cl:1][C:2]1[C:6]([CH2:7][O:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[C:20]([F:31])[C:19]=2[F:32])=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[S:4][N:3]=1

Participants

3

Reactant 2

HCID 90404786Ethyl 3-(2,3-difluoro-4-hydroxyphenyl)propanoateHCID 90418669HCID 90418669, compound

Product 1

HCID 85472224HCID 85472224, compound

Procedure

The title compound was prepared according to the procedure described in Example 127 following Steps 6 and 7 by coupling 3-chloro-4-(chloromethyl)-5-(4-ethylphenyl)isothiazole and ethyl 3-(4-hydroxy-2,3-difluorophenyl)propanoate to afford the desired product as an off-white solid. 1H NMR (300 MHz, CD3OD) δ 7.36 (d, J=8.1 Hz, 2H), 7.26 (d, J=8.1 Hz, 2H), 6.87 (t, J=8.4 Hz, 1H), 6.76 (t, J=8.7 Hz, 1H), 4.96 (s, 2H), 2.82 (t, J=7.5 Hz, 2H), 2.61 (q, J=7.5, 15.2 Hz, 2H), 2.49 (t, J=7.5 Hz, 2H), 1.15 (t, J=7.5 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for C21H18ClF2NO3S, 438.1 (M+H). found 438.1.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-fddaab9f369f471db7b627390b568ff8
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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