3-Pyridinylboronic acid → 2-Tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-4-(pyridin-3-yl)naphthalen-2-yl)acetic acid

HRID 514135Notes

Reaction equation

HRID 514135 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].[N:31]1[CH:36]=C[CH:34]=[C:33](B(O)O)[CH:32]=1>>[C:1]([O:5][CH:6]([C:12]1[C:21]([CH3:22])=[C:20]([C:23]2[CH:36]=[N:31][CH:32]=[CH:33][CH:34]=2)[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]([OH:9])=[O:8])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 67126302Ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3,4-dimethylnaphthalen-2-yl)acetate

Product 1

HCID 671262492-Tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-4-(pyridin-3-yl)naphthalen-2-yl)acetic acid

Procedure

2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-4-(pyridin-3-yl)naphthalen-2-yl)acetic acid (138) 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 pyridin-3-yl-boronic acid in the Suzuki reaction, giving the title compound (mono trifluoroacetic acid salt). 1H-NMR: (400 MHz, DMSO-d6): δ 12.8 (s, broad, 1H), 8.80 (d, J=5.1 Hz, 1H), 8.62 (d, J=12.9 Hz, 1H), 7.97-7.92 (m, 1H), 7.76-7.69 (m, 3H), 7.60-7.54 (m, 1H), 7.47-7.40 (m, 3H), 7.28 (d, J=9.2 Hz, 1H), 7.18 (d, J=9.4 Hz, 1H), 5.15 (s, 1H), 2.25 (s, 3H), 0.96 (s, 9H). 19F-NMR: (377 MHz, DMSO-d6): δ−74.7 (s) LCMS-ESI+ (m/z): [M+H]+ calcd for C28H27ClNO3: 460.2; Found: 460.2.

Workup

  1. customin the Suzuki reaction

Sources & evidence

ORD record
ord-75c1e9becbc841fa88ffaf3e2f7079a3
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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