3-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → HCID 118195141, compound

HRID 923873Notes

Reaction equation

HRID 923873 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]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[CH3:28][O:29][C:30]1[CH:31]=[N:32][CH:33]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:35]=1>>[OH:27][C@@H:24]1[CH2:25][CH2:26][N:22]([C:3]2[C:2]([C:34]3[CH:33]=[N:32][CH:31]=[C:30]([O:29][CH3:28])[CH:35]=3)=[CH:21][C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3)=[O:8])=[CH:5][N:4]=2)[CH2:23]1

Participants

3

Reactant 2

HCID 38661613-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 86702593(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118195141HCID 118195141, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 54 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 35.1) and 3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine to afford a white solid. UPLC-MS (condition 1) tR=2.10 min, m/z=475.2 [M+H]+, m/z=473.2 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.67-1.79 (m, 1H) 1.79-1.92 (m, 1H) 2.91 (d, J=11.25 Hz, 1H) 3.19-3.27 (m, 2H) 3.33-3.47 (m, 1H) 3.89 (s, 3H) 4.16-4.25 (m, 1H) 4.83 (d, J=3.42 Hz, 1H) 7.34 (d, J=8.80 Hz, 2H) 7.41 (d, J=1.96 Hz, 1H) 7.86 (d, J=9.05 Hz, 2H) 8.04 (d, J=2.45 Hz, 1H) 8.21 (d, J=1.47 Hz, 1H) 8.30 (d, J=2.69 Hz, 1H) 8.76 (d, J=2.20 Hz, 1H) 10.15 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-f009eb33f5374bc7a7e90c31cf5fbae4
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

Loading…