3-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → HCID 118195152, compound

HRID 924099Notes

Reaction equation

HRID 924099 reaction equation
Br[C:2]1[C:3]([N:23]2[CH2:27][CH2:26][C@@H:25]([OH:28])[CH2:24]2)=[N:4][CH:5]=[C:6]([CH:22]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([C:18]([F:21])([F:20])[F:19])=[O:17])=[CH:12][CH:11]=1)=[O:8].[F:29][C:30]1[CH:31]=[N:32][CH:33]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:35]=1>>[F:29][C:30]1[CH:35]=[C:34]([C:2]2[C:3]([N:23]3[CH2:27][CH2:26][C@@H:25]([OH:28])[CH2:24]3)=[N:4][CH:5]=[C:6]([C:7]([NH:9][C:10]3[CH:11]=[CH:12][C:13]([S:16]([C:18]([F:21])([F:19])[F:20])=[O:17])=[CH:14][CH:15]=3)=[O:8])[CH:22]=2)[CH:33]=[N:32][CH:31]=1

Participants

3

Reactant 2

HCID 164142683-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 89907831HCID 89907831, compound

Product 1

HCID 118195152HCID 118195152, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 185 using 5-bromo-6-((R)-3-hydroxypyrrolidin-1-yl)-N-(4-((trifluoromethyl)sulfinyl)phenyl)nicotinamide (Stage 222.1) and 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine to afford an off-white foam. HPLC (Condition 4) tR=4.46 min, UPLC-MS (Condition 3) tR=0.87 min, m/z=495.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.65-1.78 (m, 1H) 1.79-1.88 (m, 1H) 2.88 (d, J=1.00 Hz, 1H) 3.22 (m, J=4.70 Hz, 2H) 3.34-3.44 (m, 1H) 4.14-4.23 (m, 1H) 4.86 (d, J=3.52 Hz, 1H) 7.86 (d, J=8.99 Hz, 3H) 8.01-8.14 (m, 3H) 8.50 (s, 1H) 8.59 (d, J=2.74 Hz, 1H) 8.79 (d, J=2.35 Hz, 1H) 10.40 (s, 1H).

Workup

  1. customto afford an off-white foam

Sources & evidence

ORD record
ord-29a37250cd684cb08d213a3e0345abc7
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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