4-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → HCID 118195293, compound

HRID 923866Notes

Reaction equation

HRID 923866 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].[F:28][C:29]1[CH:34]=[CH:33][N:32]=[CH:31][C:30]=1B1OC(C)(C)C(C)(C)O1>>[F:28][C:29]1[CH:34]=[CH:33][N:32]=[CH:31][C:30]=1[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]([C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][C:17]([F:18])([F:20])[F:19])=[CH:14][CH:15]=2)=[O:8])[CH:21]=1

Participants

3

Reactant 2

HCID 569244444-Fluoro-3-(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 118195293HCID 118195293, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 7 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 35.1) and 4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine to afford a solid. UPLC-MS (Condition 3), tR=0.97 min, m/z=463.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6), δ ppm 1.66-1.76 (m, 1H) 1.77-1.89 (m, 1H) 2.87-2.97 (m, 1H) 3.14-3.21 (m, 1H) 3.30 (s, 2H) 4.14-4.23 (m, 1H) 4.82-4.92 (m, 1H) 7.33 (d, J=8.99 Hz, 2H) 7.41-7.49 (m, 1H) 7.83 (d, J=8.99 Hz, 2H) 8.03 (d, J=2.35 Hz, 1H) 8.61-8.67 (m, 1H) 8.68-8.77 (m, 1H) 8.79 (d, J=2.35 Hz, 1H) 10.15 (s, 1H).

Workup

  1. customto afford a solid

Sources & evidence

ORD record
ord-dbb79376f84447a8beb00387d6753289
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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