(R)-3-Pyrrolidinol → (R)-5-Bromo-N-(4-(1,1-difluoroethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide

HRID 924084Notes

Reaction equation

HRID 924084 reaction equation
[Br:1][C:2]1[C:3](Cl)=[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])[CH3:18])=[CH:12][CH:11]=1)=[O:8].[NH:23]1[CH2:27][CH2:26][C@@H:25]([OH:28])[CH2:24]1>>[Br:1][C:2]1[C:3]([N:23]2[CH2:27][CH2:26][C@@H:25]([OH:28])[CH2:24]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])[CH3:18])=[CH:12][CH:11]=1)=[O:8]

Participants

3

Reactant 2

HCID 2759337(R)-3-PyrrolidinolHCID 867026295-bromo-6-chloro-N-(4-(1,1-difluoroethoxy)phenyl)nicotinamide

Product 1

HCID 86702628(R)-5-Bromo-N-(4-(1,1-difluoroethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Stage 33.1 using 5-bromo-6-chloro-N-(4-(1,1-difluoroethoxy)phenyl)nicotinamide (Stage 215.2) and (R)-pyrrolidin-3-ol to afford a white solid. HPLC (Condition 4) tR=5.11 min, UPLC-MS (Condition 3) tR=1.02 min, m/z=440.3 [M−H]−.

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-a21cc90559294584a67a66d1dbe0bf0d
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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