(3,5-Difluorophenyl)boronic acid → HCID 89907260, compound

HRID 923879Notes

Reaction equation

HRID 923879 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[CH:30]=[C:31](B(O)O)[CH:32]=[C:33]([F:35])[CH:34]=1>>[F:28][C:29]1[CH:30]=[C:31]([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]([CH:21]=2)[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:18])[F:19])=[CH:12][CH:11]=2)=[O:8])[CH:32]=[C:33]([F:35])[CH:34]=1

Participants

3

Reactant 2

HCID 2734338(3,5-Difluorophenyl)boronic acidHCID 86702593(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 89907260HCID 89907260, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 57 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 35.1) and (3,5-difluorophenyl)boronic acid. HPLC (Condition 4) tR=5.71 min, UPLC-MS (Condition 3) tR=1.20 min, m/z=480.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.67-1.76 (m, 1H) 1.79-1.91 (m, 1H) 2.88 (d, J=11.73 Hz, 1H) 3.16-3.28 (m, 2H) 3.42 (m, J=7.00 Hz, 1H) 4.20 (m, J=2.00 Hz, 1H) 4.85 (d, J=3.52 Hz, 1H) 7.15 (dd, J=8.21, 1.95 Hz, 2H) 7.21-7.29 (m, 1H) 7.33 (d, J=8.99 Hz, 2H) 7.78-7.90 (m, 2H) 8.02 (d, J=2.35 Hz, 1H) 8.74 (d, J=2.35 Hz, 1H) 10.15 (s, 1H).

Sources & evidence

ORD record
ord-59daf9b531284b43b19d5072a2fbeef0
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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