4-Fluorophenylboronic acid → n-(2-Cyclopropyl-2-hydroxy-propyl)-6-(cyclopropylmethyl-methyl-amino)-5-(4-fluoro-phenyl)-nicotinamide

HRID 1159263Notes

Reaction equation

HRID 1159263 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[C:7](Cl)=[N:6][CH:5]=1.Cl.[CH:14]1([CH2:17][NH:18][CH3:19])[CH2:16][CH2:15]1.[F:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.[NH2:30][CH2:31][C:32]([CH:35]1[CH2:37][CH2:36]1)([OH:34])[CH3:33]>>[CH:35]1([C:32]([OH:34])([CH3:33])[CH2:31][NH:30][C:3](=[O:12])[C:4]2[CH:9]=[C:8]([C:24]3[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=3)[C:7]([N:18]([CH2:17][CH:14]3[CH2:16][CH2:15]3)[CH3:19])=[N:6][CH:5]=2)[CH2:37][CH2:36]1

Participants

5

Reactant 4

HCID 2856454-Fluorophenylboronic acidHCID 2764313Methyl 5-bromo-6-chloronicotinateHCID 12919210(Cyclopropylmethyl)(methyl)amine hydrochlorideHCID 211096921-Amino-2-cyclopropylpropan-2-ol

Product 1

HCID 24856755n-(2-Cyclopropyl-2-hydroxy-propyl)-6-(cyclopropylmethyl-methyl-amino)-5-(4-fluoro-phenyl)-nicotinamide

Procedure

The title compound was synthesized in analogy to the procedure described for the preparation of Example 43, using 5-bromo-6-chloro-nicotinic acid methyl ester, cyclopropylmethyl methylamine hydrochloride, (commercially available), 4-fluorophenyl-boronic acid (commercially available) and rac-1-amino-2-cyclopropyl-propan-2-ol (commercially available) as starting materials. MS (ISP): 398.0 (M+H+).

Workup

  1. customdescribed for the preparation of Example 43

Sources & evidence

ORD record
ord-54a2d077cd30434ebaccf4a0002d8519
Source dataset
uspto-grants-2010_10
Patent number
US07812028B2

Reaction notes

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