2-Chloro-5-fluoropyridine-3-boronic acid pinacol ester → HCID 118195348, compound

HRID 924149Notes

Reaction equation

HRID 924149 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[Cl:28][C:29]1[C:34](B2OC(C)(C)C(C)(C)O2)=[CH:33][C:32]([F:44])=[CH:31][N:30]=1>>[Cl:28][C:29]1[C:34]([C:2]2[C:3]([N:22]3[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]3)=[N:4][CH:5]=[C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=3)=[O:8])[CH:21]=2)=[CH:33][C:32]([F:44])=[CH:31][N:30]=1

Participants

3

Reactant 2

HCID 533983702-Chloro-5-fluoropyridine-3-boronic acid pinacol esterHCID 72545856(R)-5-Bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide

Product 1

HCID 118195348HCID 118195348, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 287 using (R)-5-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide (Stage 171.1) and 2-chloro-5-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine to afford a slightly rose powder. UPLC-MS (Condition 3), tR=1.09 min, m/z=513.2/515.1 [M+H]+; 1H-NMR (600 MHz, DMSO-d6) δ ppm 1.67-1.96 (m, 2H) 2.86-3.50 (m, 4H) 4.14-4.29 (m, 1H) 7.33 (d, J=8.78 Hz, 2H) 7.85 (d, J=9.15 Hz, 2H) 7.97-8.02 (m, 1H) 8.02-8.21 (m, J=8.42, 2.93 Hz, 1H) 8.55 (t, J=3.11 Hz, 1H) 8.81 (dd, J=7.68, 2.20 Hz, 1H) 10.17 (s, 1H).

Workup

  1. customto afford a slightly rose powder

Sources & evidence

ORD record
ord-663c04f250c048e39508364fdda2b360
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

Loading…