4-Chlorophenylboronic acid → Nicotinamide

HRID 1766492Notes

Reaction equation

HRID 1766492 reaction equation
BrC1C(Cl)=[N:4]C=C(C)C=1.OCC1CC1.ClC1C=CC(B(O)O)=CC=1.[NH2:25][CH2:26][C@H:27]1[CH2:32][CH2:31][CH2:30]C[C@H:28]1[OH:33]>>[C:28]([NH2:4])(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[N:25][CH:26]=1

Participants

5

Reactant 4

HCID 742994-Chlorophenylboronic acidHCID 75644CyclopropanemethanolHCID 2854373-Bromo-2-chloro-5-methylpyridineHCID 12483365cis-2-Aminomethyl-1-cyclohexanol

Product 1

HCID 936Nicotinamide

Procedure

The title compound was synthesized in analogy to Example 2, using 3-bromo-2-chloro-5-methyl-pyridine, hydroxymethylcyclopropane, [4-chloro-phenyl]-boronic acid and cis-2-aminomethyl-1-cyclohexanol as starting materials to yield racemic cis-5-(4-chloro-phenyl)-6-cyclopropylmethoxy-N-2-hydroxy-cyclohexylmethyl)-nicotinamide. Separation with heptane/ethanol on ChiralpakAD® yielded the (−)-enantiomer, MS (ISP) 415.2 (M+H)+, αD20: −17.8° in MeOH.

Sources & evidence

ORD record
ord-ea02a304e1354ed693ad299330ccb763
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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