(5-Fluoropyridin-3-yl)boronic acid → HCID 118195175, compound

HRID 924075Notes

Reaction equation

HRID 924075 reaction equation
Br[C:2]1[C:3]([N:24]2[CH2:28][CH2:27][C@@H:26]([OH:29])[CH2:25]2)=[N:4][CH:5]=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[F:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[N:35][CH:36]=1>>[F:30][C:31]1[CH:32]=[C:33]([C:2]2[C:3]([N:24]3[CH2:28][CH2:27][C@@H:26]([OH:29])[CH2:25]3)=[N:4][CH:5]=[C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3)=[O:8])[CH:23]=2)[CH:34]=[N:35][CH:36]=1

Participants

3

Reactant 2

HCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 86702613HCID 86702613, compound

Product 1

HCID 118195175HCID 118195175, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 151 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(perfluoroethyl)phenyl)nicotinamide (Stage 208.1) and (5-fluoropyridin-3-yl)boronic acid to afford a beige solid. UPLC-MS (Condition 3) tR=1.10 min, m/z=497.4 [M+H]+, m/z=495.3 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.69-1.79 (m, 1H) 1.85 (m, J=9.05 Hz, 1H) 2.88 (d, J=11.25 Hz, 1H) 3.18-3.29 (m, 2H) 3.35-3.46 (m, 1H) 4.16-4.26 (m, 1H) 4.87 (d, J=3.42 Hz, 1H) 7.67 (d, J=8.80 Hz, 2H) 7.84 (dt, J=9.66, 2.26 Hz, 1H) 8.00 (d, J=8.80 Hz, 2H) 8.09 (d, J=2.20 Hz, 1H) 8.49-8.53 (m, 1H) 8.60 (d, J=2.93 Hz, 1H) 8.80 (d, J=2.20 Hz, 1H) 10.33 (s, 1H).

Workup

  1. customto afford a beige solid

Sources & evidence

ORD record
ord-f780719fe2cf443da0603c8cac6f8e99
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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