Cyclopropanemethanol → 6-cyclopropylmethoxy-5-(4-fluoro-phenyl)-N-(2-hydroxy-2-methyl-propyl)-nicotinamide

HRID 1159284Notes

Reaction equation

HRID 1159284 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([OH:11])=O)[CH:5]=[N:6][C:7]=1Cl.[OH:12][CH2:13][CH:14]1[CH2:16][CH2:15]1.[F:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.Cl.[NH2:28][CH2:29][C:30]([CH3:33])([OH:32])[CH3:31]>>[CH:14]1([CH2:13][O:12][C:7]2[C:2]([C:21]3[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=3)=[CH:3][C:4]([C:9]([NH:28][CH2:29][C:30]([OH:32])([CH3:33])[CH3:31])=[O:11])=[CH:5][N:6]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 4

HCID 75644CyclopropanemethanolHCID 2854335-Bromo-6-chloropyridine-3-carboxylic acidHCID 2856454-Fluorophenylboronic acidHCID 123861811-Amino-2-methyl-propan-2-ol hydrochloride

Product 1

HCID 211096566-cyclopropylmethoxy-5-(4-fluoro-phenyl)-N-(2-hydroxy-2-methyl-propyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to Example 31, using 5-bromo-6-chloro-3-pyridinecarboxylic acid, hydroxymethyl-cyclopropan, 4-fluorophenylboronic acid and 1-amino-2-methyl-propan-2-ol hydrochloride as starting materials to yield 6-cyclopropylmethoxy-5-(4-fluoro-phenyl)-N-(2-hydroxy-2-methyl-propyl)-nicotinamide. MS (ISP) 359.1 (M+H)+.

Workup

  1. customThe title compound was synthesized in analogy to Example 31

Sources & evidence

ORD record
ord-064579c2c0144605b762b31d766bf508
Source dataset
uspto-grants-2010_10
Patent number
US07812028B2

Reaction notes

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