[3-Fluoro-5-(methoxycarbonyl)phenyl]boronic acid → HCID 118198931, compound

HRID 923880Notes

Reaction equation

HRID 923880 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]([C:35]([O:37][CH3:38])=[O:36])[CH:34]=1>>[F:28][C:29]1[CH:34]=[C:33]([CH:32]=[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]([C:7](=[O:8])[NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:19])([F:20])[F:18])=[CH:12][CH:11]=3)[CH:21]=2)[CH:30]=1)[C:35]([O:37][CH3:38])=[O:36]

Participants

3

Reactant 2

HCID 44717206[3-Fluoro-5-(methoxycarbonyl)phenyl]boronic acidHCID 86702593(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118198931HCID 118198931, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 35 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 35.1) and (3-fluoro-5-(methoxycarbonyl)phenyl)boronic acid to afford a white solid. UPLC-MS (Condition 3), tR=1.18 min, m/z=520.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6), δ ppm 1.67-1.75 (m, 1H) 1.77-1.89 (m, 1H) 2.81-2.90 (m, 1H) 3.13-3.27 (m, 2H) 3.33-3.45 (m, 1H) 3.88 (s, 3H) 4.13-4.20 (m, 1H) 4.82 (d, J=1.00 Hz, 1H) 7.33 (d, J=8.60 Hz, 2H) 7.54-7.63 (m, 1H) 7.65-7.73 (m, 1H) 7.74-7.79 (m, 1H) 7.84 (d, J=9.38 Hz, 2H) 8.03 (d, J=2.35 Hz, 1H) 8.75 (d, J=2.35 Hz, 1H) 10.17 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-3144ff38c7f3441791d52f591be3372d
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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