Water → N-(4-fluorophenyl)pyridine-3-carboxamide

HRID 404757Notes

Reaction equation

HRID 404757 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][C:13](S)=[N:12][CH:11]=2)=[CH:4][CH:3]=1.BrCC1C=CC(OC(F)(F)F)=CC=1B(O)O.CCN(C(C)C)C(C)C.O>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 675401372-Bromomethyl-5-trifluoromethoxy-phenylboronic acidHCID 178522139HCID 178522139, compound

Product 1

HCID 279881N-(4-fluorophenyl)pyridine-3-carboxamideYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

As described in Method B, N-(4-fluoro-phenyl)-6-mercapto-nicotinamide IIa (372 mg, 1.5 mmol) and 2-bromomethyl-5-trifluoromethoxy-phenylboronic acid (572 mg, 1.5 mmol) were suspended in DMF (15 ml). To the reaction flask DIPEA (261 μL, 1.5 mmol) was added and the reaction was stirred for 30 minutes. Reaction completion was monitored by LC-MS. Cold water (100 mL) was added and the precipitate was collected by filtration and washed several times with cold water to afford 724.8 mg (88% yield, >90% purity by LC-MS) of the off-white solid product, 6-(2-boronic pinacol ester-5-trifluoromethoxy-benzylsulfanyl)-N-(4-fluoro-phenyl)-nicotinamide. ESI-MS m/z=549.1 [M+H+].

Workup

  1. customReaction completion
  2. filtrationthe precipitate was collected by filtration
  3. washwashed several times with cold water

Sources & evidence

ORD record
ord-5c81e7fbf501430897abb65457339427
Source dataset
uspto-grants-2014_06
Patent number
US08748623B2

Reaction notes

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