3-Fluorophenylboronic acid → HCID 118195273, compound

HRID 923876Notes

Reaction equation

HRID 923876 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]=[CH:33][CH:34]=1>>[F:28][C:29]1[CH:34]=[C:33]([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:19])[F:18])=[CH:12][CH:11]=2)=[O:8])[CH:32]=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 27339863-Fluorophenylboronic acidHCID 86702593(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118195273HCID 118195273, 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-fluorophenyl)boronic acid to afford an off-white solid. HPLC (Condition 4) tR=5.48 min, UPLC-MS (Condition 3) tR=1.17 min, m/z=462.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.72 (m, J=3.90 Hz, 1H) 1.77-1.89 (m, 1H) 2.86 (d, J=11.34 Hz, 1H) 3.12-3.27 (m, 2H) 3.40 (m, J=7.40 Hz, 1H) 4.09-4.22 (m, 1H) 4.82 (d, J=3.52 Hz, 1H) 7.15-7.28 (m, 3H) 7.34 (d, J=1.00 Hz, 2H) 7.41-7.53 (m, 1H) 7.77-7.90 (m, 2H) 7.99 (d, J=2.30 Hz, 1H) 8.73 (d, J=2.35 Hz, 1H) 10.15 (s, 1H).

Workup

  1. customto afford an off-white solid

Sources & evidence

ORD record
ord-256d24cbebcc40a0aa39a5ae96e8da11
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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