3-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → HCID 118195264, compound

HRID 924078Notes

Reaction equation

HRID 924078 reaction equation
Br[C:2]1[C:3]([N:24]2[CH2:28][CH2:27][C@@H:26]([OH:29])[CH2:25]2)=[N:4][CH:5]=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:22])([F:21])[CH:18]([F:20])[F:19])=[CH:12][CH:11]=1)=[O:8].[F:30][C:31]1[CH:32]=[N:33][CH:34]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH:36]=1>>[F:30][C:31]1[CH:36]=[C:35]([C:2]2[C:3]([N:24]3[CH2:28][CH2:27][C@@H:26]([OH:29])[CH2:25]3)=[N:4][CH:5]=[C:6]([C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([O:16][C:17]([F:22])([F:21])[CH:18]([F:19])[F:20])=[CH:14][CH:15]=3)=[O:8])[CH:23]=2)[CH:34]=[N:33][CH:32]=1

Participants

3

Reactant 2

HCID 164142683-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 118195167HCID 118195167, compound

Product 1

HCID 118195264HCID 118195264, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 151 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(1,1,2,2-tetrafluoroethoxy)phenyl)nicotinamide (Stage 212.1) and 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine to afford a solid. UPLC-MS (Condition 3), tR=0.96 min, m/z=495.3; 1H-NMR (400 MHz, DMSO-d6), δ ppm 1.75 (br. s, 1H) 1.86 (d, J=8.21 Hz, 1H) 2.88 (d, J=12.12 Hz, 1H) 3.17-3.29 (m, 3H) 3.35-3.46 (m, 1H) 4.21 (br. s, 1H) 4.88 (br. s, 1H) 6.79 (m, 1H) 7.26 (d, J=8.99 Hz, 2H) 7.83 (d, J=9.38 Hz, 3H) 8.08 (d, J=2.35 Hz, 1H) 8.51 (s, 1H) 8.60 (d, J=2.74 Hz, 1H) 8.76-8.81 (m, 1H) 10.15 (s, 1H).

Workup

  1. customto afford a solid

Sources & evidence

ORD record
ord-8b9c287f041242ce88192738fc5548ee
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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