4-Chlorophenylboronic acid → HCID 90418054, compound

HRID 2177315Notes

Reaction equation

[Cl:1]C1C=CC(B(O)O)=CC=1.[C:11]1(C)[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[S:21][N:20]=[C:19]([C:22]([F:25])([F:24])[F:23])[C:18]=1[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][C:36]([O:38]CC)=[O:37])=[C:30]([Cl:41])[CH:29]=1>>[Cl:41][C:30]1[CH:29]=[C:28]([O:27][CH2:26][C:18]2[C:19]([C:22]([F:24])([F:25])[F:23])=[N:20][S:21][C:17]=2[C:12]2[CH:13]=[CH:14][C:15]([Cl:1])=[CH:16][CH:11]=2)[CH:33]=[CH:32][C:31]=1[CH2:34][CH2:35][C:36]([OH:38])=[O:37]

Participants

Reactant 2

HCID 742994-Chlorophenylboronic acid

HCID 90418690HCID 90418690, compound

Product 1

HCID 90418054HCID 90418054, compound

Procedure

The title compound was prepared according to the procedure described in Example 172 following Step 1-6 using (4-chloro-phenyl)boronic acid for coupling and then hydrolysis of ethyl 3-(4-((5-(o-tolyl)-3-(trifluoromethyl)isothiazol-4-yl)methoxy)-2-chloro-phenyl)propanoate to afford the desired product as an off-white solid. 1H NMR (300 MHz, CD3OD) δ7.53-7.59 (m, 4H), 7.25 (d, J=8.4 Hz, 1H), 6.97 (s, 1H), 6.81-6.85 (m, 1H), 5.06 (s, 2H), 2.99 (t, J=8.1 Hz, 2H), 2.60 (t, J=8.1 Hz, 2H). Mass spectrum (ESI, m/z): Calcd. for C20H14Cl2F3NO3S, 474.0 (M−H). found 474.0.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-efe06f3fa17844bc9dc73ec6c72f9065
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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