2-Methylpyridine-5-boronic acid → HCID 118195160, compound

HRID 923847Notes

Reaction equation

HRID 923847 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][CH: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][C:29]1[N:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1>>[OH:27][CH:24]1[CH2:25][CH2:26][N:22]([C:3]2[C:2]([C:32]3[CH:33]=[N:34][C:29]([CH3:28])=[CH:30][CH:31]=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 27630812-Methylpyridine-5-boronic acidHCID 89904540HCID 89904540, compound

Product 1

HCID 118195160HCID 118195160, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 28 using 5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 12.1) and (6-methylpyridin-3-yl)boronic acid to afford an off-white solid. UPLC-MS (condition 1) tR=1.61 min, m/z=459.0 [M+H]+, m/z=457.2 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.67-1.77 (m, 1H) 1.77-1.88 (m, 1H) 2.53 (s, 3H) 2.88 (d, J=11.49 Hz, 1H) 3.15-3.27 (m, 2H) 3.38 (td, J=9.96, 7.21 Hz, 1H) 4.15-4.22 (m, 1H) 4.84 (d, J=3.42 Hz, 1H) 7.34 (d, J=8.07 Hz, 3H) 7.68 (dd, J=7.95, 2.32 Hz, 1H) 7.85 (d, J=9.05 Hz, 2H) 7.99 (d, J=2.45 Hz, 1H) 8.48 (d, J=2.20 Hz, 1H) 8.75 (d, J=2.45 Hz, 1H) 10.15 (s, 1H).

Workup

  1. customto afford an off-white solid

Sources & evidence

ORD record
ord-ad5aa4bff1b14a2d8750ea7184279e04
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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