(3-Cyano-5-fluorophenyl)boronic acid → HCID 89907725, compound

HRID 924154Notes

Reaction equation

HRID 924154 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]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[C:28]([C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[C:34]([F:36])[CH:35]=1)#[N:29]>>[Cl:20][C:17]([F:19])([F:18])[O:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:21]=[C:2]([C:32]3[CH:33]=[C:34]([F:36])[CH:35]=[C:30]([C:28]#[N:29])[CH:31]=3)[C:3]([N:22]3[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]3)=[N:4][CH:5]=2)=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 23435605(3-Cyano-5-fluorophenyl)boronic acidHCID 72545856(R)-5-Bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide

Product 1

HCID 89907725HCID 89907725, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 290 using (R)-5-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide (Stage 171.1) and 3-Cyano-5-Fluorophenylboronic acid to afford a white solid. HPLC (Condition 10) tR=6.383 min, UPLC-MS (Condition 11) m/z=503.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.69-1.80 (m, 1H) 1.81-1.93 (m, 1H) 2.86 (d, J=10.95 Hz, 1H) 3.14-3.29 (m, 2H) 3.35-3.49 (m, 1H) 4.21 (br. s, 1H) 4.87 (d, J=3.52 Hz, 1H) 7.34 (d, J=8.60 Hz, 2H) 7.67 (d, J=9.38 Hz, 1H) 7.79 (s, 1H) 7.83-7.91 (m, J=8.99 Hz, 3H) 8.06 (d, J=1.96 Hz, 1H) 8.77 (d, J=2.35 Hz, 1H) 10.17 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-e6b803b46a4645fd862213d8b50a4156
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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