3-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → HCID 118195233, compound

HRID 924098Notes

Reaction equation

HRID 924098 reaction equation
Br[C:2]1[C:3]([N:25]2[CH2:29][CH2:28][C@@H:27]([OH:30])[CH2:26]2)=[N:4][CH:5]=[C:6]([CH:24]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])=[CH:12][CH:11]=1)=[O:8].[F:31][C:32]1[CH:33]=[N:34][CH:35]=[C:36](B2OC(C)(C)C(C)(C)O2)[CH:37]=1>>[F:31][C:32]1[CH:37]=[C:36]([C:2]2[C:3]([N:25]3[CH2:29][CH2:28][C@@H:27]([OH:30])[CH2:26]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:23])([F:22])[C:18]([F:20])([F:21])[F:19])=[CH:14][CH:15]=3)=[O:8])[CH:24]=2)[CH:35]=[N:34][CH:33]=1

Participants

3

Reactant 2

HCID 164142683-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 86702619(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(perfluoroethoxy)phenyl)nicotinamide

Product 1

HCID 118195233HCID 118195233, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 185 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(perfluoroethoxy)phenyl)nicotinamide (Stage 220.1) 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=5.58 min, UPLC-MS (Condition 3) tR=1.07 min, m/z=513.4 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.67-1.76 (m, 1H) 1.78-1.89 (m, 1H) 2.86 (d, J=11.34 Hz, 1H) 3.13-3.26 (m, 2H) 3.33-3.43 (m, 1H) 4.19 (br. s, 1H) 4.85 (d, J=3.13 Hz, 1H) 7.33 (d, J=8.99 Hz, 2H) 7.76-7.90 (m, 3H) 8.03-8.09 (m, 1H) 8.49 (s, 1H) 8.58 (d, J=2.74 Hz, 1H) 8.72-8.82 (m, 1H) 8.99-9.00 (m, OH) 10.16 (s, 1H).

Workup

  1. customto afford an off-white foam

Sources & evidence

ORD record
ord-f9052f270a82421681d3a689189110a6
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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