(5-Fluoropyridin-3-yl)boronic acid → HCID 118195345, compound

HRID 924070Notes

Reaction equation

HRID 924070 reaction equation
Br[C:2]1[C:3]([N:23]2[CH2:27][CH2:26][C@@H:25]([OH:28])[CH2:24]2)=[N:4][CH:5]=[C:6]([CH:22]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][C:17]([F:20])([F:19])[F:18])=[C:12]([F:21])[CH:11]=1)=[O:8].[F:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[N:34][CH:35]=1>>[F:29][C:30]1[CH:31]=[C:32]([C:2]2[C:3]([N:23]3[CH2:27][CH2:26][C@@H:25]([OH:28])[CH2:24]3)=[N:4][CH:5]=[C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([S:16][C:17]([F:19])([F:20])[F:18])=[C:12]([F:21])[CH:11]=3)=[O:8])[CH:22]=2)[CH:33]=[N:34][CH:35]=1

Participants

3

Reactant 2

HCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 86702610(R)-5-bromo-N-(3-fluoro-4-((trifluoromethyl)thio)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide

Product 1

HCID 118195345HCID 118195345, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 151 using (R)-5-bromo-N-(3-fluoro-4-((trifluoromethyl)thio)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide (Stage 205.1) and (5-fluoropyridin-3-yl)boronic acid to afford a yellow wax which slowly crystallized upon drying. UPLC-MS (Condition 3) tR=1.12 min, m/z=497.3 [M+H]+, m/z=495.3 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.67-1.79 (m, 1H) 1.84 (qd, J=8.43, 4.33 Hz, 1H) 2.88 (d, J=11.42 Hz, 1H) 3.18-3.29 (m, 2H) 3.34-3.47 (m, 1H) 4.14-4.27 (m, 1H) 4.88 (d, J=3.39 Hz, 1H) 7.67 (dd, J=8.66, 2.01 Hz, 1H) 7.75 (t, J=8.41 Hz, 1H) 7.84 (dt, J=9.72, 2.10 Hz, 1H) 7.97 (dd, J=11.73, 2.07 Hz, 1H) 8.07 (d, J=2.38 Hz, 1H) 8.48-8.54 (m, 1H) 8.60 (d, J=2.76 Hz, 1H) 8.79 (d, J=2.26 Hz, 1H) 10.45 (s, 1H).

Workup

  1. customto afford a yellow wax which
  2. customslowly crystallized
  3. customupon drying

Sources & evidence

ORD record
ord-297c61d6aed945f9a9766dd92429ec17
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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