2,5-Difluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → HCID 118195320, compound

HRID 923867Notes

Reaction equation

HRID 923867 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[C:34](B2OC(C)(C)C(C)(C)O2)=[CH:33][C:32]([F:44])=[CH:31][N:30]=1>>[F: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]([F: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 532167702,5-Difluoro-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 118195320HCID 118195320, 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 2,5-difluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine to afford a solid. UPLC-MS (Condition 3), tR=1.05 min, m/z=481.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6), δ ppm 1.78 (br. s, 1H) 1.87 (br. s, 1H) 2.97 (br. s, 1H) 3.17-3.29 (m, 2H) 3.42 (dd, J=16.03, 7.04 Hz, 1H) 4.23 (br. s, 1H) 4.91 (br. s, 1H) 7.35 (m, J=8.60 Hz, 2H) 7.50 (br. s, 1H) 7.85 (m, J=8.99 Hz, 2H) 8.05-8.13 (m, 1H) 8.28-8.39 (m, 1H) 8.74-8.86 (m, 1H) 10.18 (s, 1H).

Workup

  1. customto afford a solid

Sources & evidence

ORD record
ord-f0ceb1c662484a48a9d6e9522b9284e5
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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