2-Chloro-3-pyridinecarboxaldehyde → 2-((4-Fluorophenyl)sulfonyl)nicotinaldehyde

HRID 41868

Reaction equation

Cl[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Na+].[F:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([O-:20])=[O:19])=[CH:14][CH:13]=1>CS(C)=O.O>[F:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([C:2]2[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-Chloro-3-pyridinecarboxaldehyde (4.04 g, 2.86 mmol) and 4-fluorobenzenesulfinic acid sodium salt (5.73 g, 3.14 mmol) were dissolved in DMSO (100 ml) and the mixture was heated at 100° C. for 72 h under nitrogen. Upon cooling to ambient the mixture was diluted with water (500 ml) and extracted with EtOAc (3×). The combined organics were washed with water, brine, dried (MgSO4) and evaporated to dryness to afford 7.89 g of crude product. The crude compound was pre-absorbed onto silica and purified by dry pad suction column chromatography, eluting with heptane using an EtOAc gradient, to afford 4.14 g (41%) of the desired product as a yellow solid (plates) (MP=131-131.3° C.; IR=1691 cm−1; HPLC=7.21 min>99%).

Workup

temperatureUpon cooling to ambient the mixture
extractionextracted with EtOAc (3×)
washThe combined organics were washed with water, brine
dry with materialdried (MgSO4)
customevaporated to dryness
customto afford 7.89 g of crude product
customThe crude compound was pre-absorbed onto silica
custompurified
customby dry pad suction column chromatography
washeluting with heptane using an EtOAc gradient

Sources & evidence

ORD record: ord-d367e75b4b36450895f3a8ff88c05948
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536158B2

Linked notes

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