2-Fluoropyridine-3-boronic acid → HCID 118195383, compound

HRID 924021Notes

Reaction equation

HRID 924021 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].[F:28][C:29]1[C:34](B(O)O)=[CH:33][CH:32]=[CH:31][N:30]=1>>[Cl:20][C:17]([F:19])([F:18])[O:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7]([C:6]2[CH:21]=[C:2]([C:34]3[C:29]([F:28])=[N:30][CH:31]=[CH:32][CH:33]=3)[C:3]([N:22]3[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]3)=[N:4][CH:5]=2)=[O:8])=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 27832702-Fluoropyridine-3-boronic acidHCID 72545856(R)-5-Bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide

Product 1

HCID 118195383HCID 118195383, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 133 using (R)-5-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide (Stage 171.1) and (2-fluoropyridin-3-yl)boronic acid to afford a white solid. HPLC (Condition 4) tR=5.22 min, UPLC-MS (Condition 3) tR=1.07 min, m/z=479.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.63-1.76 (m, 1H) 1.78-1.88 (m, 1H) 2.84-2.97 (m, 1H) 3.15 (m, J=4.70 Hz, 2H) 3.31-3.43 (m, 1H) 4.14-4.24 (m, 1H) 4.86 (br. s, 1H) 7.32 (d, J=8.99 Hz, 2H) 7.42-7.54 (m, 1H) 7.76-7.89 (m, 2H) 8.00 (d, J=2.35 Hz, 1H) 8.03-8.13 (m, 1H) 8.28 (d, J=4.69 Hz, 1H) 8.78 (d, J=2.35 Hz, 1H) 10.15 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-94d53177448a40f982509f47e26e6bf2
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

Loading…