4-Chlorophenylboronic acid → 2-(1,4-Bis(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetic acid

HRID 514137Notes

Reaction equation

HRID 514137 reaction equation
[C:1]([O:5][CH:6]([C:12]1[C:21]([CH3:22])=[C:20]([CH3:23])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[Cl:31][C:32]1[CH:37]=[CH:36]C(B(O)O)=[CH:34][CH:33]=1>>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]([C:23]3[CH:36]=[CH:37][C:32]([Cl:31])=[CH:33][CH:34]=3)=[C:21]([CH3:22])[C:12]=2[CH:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])[C:7]([OH:9])=[O:8])=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 67126302Ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3,4-dimethylnaphthalen-2-yl)acetate

Product 1

HCID 680857692-(1,4-Bis(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetic acid

Procedure

2-(1,4-bis(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetic acid (140) was prepared in a manner similar to 2-tert-butoxy-2-(1-(4-chlorophenyl)-3,4-dimethylnaphthalen-2-yl)acetic acid of Example 125, except using 4-chlorobenzene boronic acid in the Suzuki reaction, giving the title compound (mono trifluoroacetic acid salt). 1H-NMR: (400 MHz, DMSO-d6): δ 12.82 (s, 1H), 7.75-7.63 (m, 4H), 7.55 (dd, J=8.2, 2.4 Hz, 1H), 7.46-7.31 (m, 5H), 7.26-7.21 (m, 2H), 5.14 (s, 1H), 2.24 (s, 3H), 0.96 (s, 9H). LCMS-ESI− (m/z): [2M-2H+Na]− calcd for C58H50Cl4NaO6: 1007.2; Found: 1007.1.

Workup

  1. customin the Suzuki reaction

Sources & evidence

ORD record
ord-b375eab45b4d486b80527fe7cb600026
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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