3-Pyridinylboronic acid → 4-((3S,4S)-3,4-Dihydroxypyrrolidin-1-yl)-3-(pyridin-3-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

HRID 923837Notes

Reaction equation

HRID 923837 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[N:22]1[CH2:26][C@H:25]([OH:27])[C@@H:24]([OH:28])[CH2:23]1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)=[O:6].[N:29]1[CH:34]=[CH:33][CH:32]=[C:31](B(O)O)[CH:30]=1>>[OH:28][C@@H:24]1[C@@H:25]([OH:27])[CH2:26][N:22]([C:21]2[CH:20]=[CH:19][C:4]([C:5]([NH:7][C:8]3[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=3)=[O:6])=[CH:3][C:2]=2[C:31]2[CH:30]=[N:29][CH:34]=[CH:33][CH:32]=2)[CH2:23]1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 899064793-Bromo-4-((3 S,4S)-3,4-dihydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

Product 1

HCID 1181952924-((3S,4S)-3,4-Dihydroxypyrrolidin-1-yl)-3-(pyridin-3-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 7 using 3-bromo-4-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 7.1) and pyridin-3-ylboronic acid to afford a yellow solid. UPLC-MS (condition 1) tR=1.67 min, m/z=460.0 [M+H]+, m/z=458.0 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.73 (d, J=10.76 Hz, 2H) 3.24 (dd, J=10.51, 3.67 Hz, 2H) 3.85 (d, J=2.20 Hz, 2H) 5.03 (br. s, 2H) 6.92 (d, J=8.80 Hz, 1H) 7.33 (d, J=8.31 Hz, 2H) 7.48 (dd, J=7.46, 5.26 Hz, 1H) 7.76-7.83 (m, 2H) 7.83-7.89 (m, 2H) 7.91 (dd, J=8.80, 2.20 Hz, 1H) 8.55 (dd, J=4.77, 1.59 Hz, 1H) 8.62 (d, J=1.47 Hz, 1H) 10.10 (s, 1H).

Workup

  1. customto afford a yellow solid

Sources & evidence

ORD record
ord-06aa3a5f577a4dd9ac8b2f1e4f55db97
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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