3-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → HCID 118195304, compound

HRID 923973Notes

Reaction equation

HRID 923973 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:25][CH:24]([CH2:26][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:30]=[N:31][CH:32]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:34]=1>>[F:28][C:29]1[CH:34]=[C:33]([C:2]2[C:3]([N:22]3[CH2:23][CH:24]([CH2:26][OH:27])[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:19])([F:18])[F:20])=[CH:14][CH:15]=3)=[O:8])[CH:21]=2)[CH:32]=[N:31][CH:30]=1

Participants

3

Reactant 2

HCID 164142683-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 899079805-bromo-6-(3-(hydroxymethyl)azetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118195304HCID 118195304, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 128 using 5-bromo-6-(3-(hydroxymethyl)azetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 135.1) and 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine. HPLC (Condition 4) tR=5.02 min, UPLC-MS (Condition 3) tR=1.01 min, m/z=463.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.56-2.68 (m, 1H) 3.37-3.52 (m, 4H) 3.71 (t, J=8.60 Hz, 2H) 4.68 (t, J=1.00 Hz, 1H) 7.34 (d, J=8.60 Hz, 2H) 7.77-7.90 (m, 3H) 8.04 (d, J=2.35 Hz, 1H) 8.49-8.55 (m, 1H) 8.60 (d, J=2.74 Hz, 1H) 8.76 (d, J=2.35 Hz, 1H) 10.18 (s, 1H).

Sources & evidence

ORD record
ord-fa2c057f1f014303938f56a3c1cffaaa
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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