Ethyl 3-(2,3-difluoro-4-hydroxyphenyl)propanoate → HCID 85472984, compound

HRID 2177335Notes

Reaction equation

[Cl:1][C:2]1[S:6][C:5]([CH2:7][OH:8])=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[CH:3]=1.O[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])=[C:20](F)[C:19]=1[F:32].ClC1SC(COC2C=C([F:47])C(CCC(OCC)=O)=C(F)C=2)=C(C2C=CC(Cl)=CC=2)C=1>>[Cl:1][C:2]1[S:6][C:5]([CH2:7][O:8][C:18]2[C:19]([F:32])=[CH:20][C:21]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:22][C:23]=2[F:47])=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[CH:3]=1

Participants

Reactant 3

HCID 90404786Ethyl 3-(2,3-difluoro-4-hydroxyphenyl)propanoate

HCID 90418025HCID 90418025, compound

HCID 90418608HCID 90418608, compound

Product 1

HCID 85472984HCID 85472984, compound

Procedure

The title compound was prepared according to the procedure described in Example 197 by coupling of [5-chloro-3-(4-ethylphenyl)thiophen-2-yl]methanol and ethyl 3-(4-hydroxy-2,3-difluorophenyl)propanoate followed by hydrolysis of ethyl 3-(4-((5-chloro-3-(4-chlorophenyl)thiophen-2-yl)methoxy)-2,6-difluorophenyl)propanoate to afford the desired product as an off-white solid. 1H-NMR (300 MHz, CD3OD) δ 7.34 (d, J=8.1 Hz, 2H), 7.24 (d, J=8.1 Hz, 2H), 7.01 (s, 1H), 6.85 (d, J=9.3 Hz, 2H), 5.11 (s, 2H), 2.87 (t, J=7.2 Hz, 2H), 2.59-2.73 (m, 4H), 1.27 (t, J=7.8 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for C22H19C1F2O3S, 435.1 (M−H). found 435.1.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-ee4ea421f6194e99917d04b763160c22
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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