Pyridine → HCID 86653631, compound

HRID 2368208Notes

Reaction equation

N1C=CC=CC=1.[S:7]([O:14]S(C(F)(F)F)(=O)=O)([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8].[C:22]([O:26][C:27]([C:29]1([CH2:38]O)[CH2:34][CH2:33][N:32]([C:35](=[O:37])[CH3:36])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>C(Cl)Cl>[C:22]([O:26][C:27]([C:29]1([CH2:38][O:14][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])[CH2:34][CH2:33][N:32]([C:35](=[O:37])[CH3:36])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

Conditions

Temperature: -78 °C

Procedure

A mixture of 2.0 ml (250 mmol) of pyridine and of 20 ml of dichloromethane is cooled to −78° C. under nitrogen. Triflic anhydride (2.10 ml, 12.5 mmol) is added drop by drop. After 10 min, a solution of 1.29 g of the compound from step 2 (5.0 mmol) in 15 ml of CH2Cl2 is added drop by drop. The mixture is stirred for 2 hours at −78° C. The organic phase is washed with 1N HCl, H2O, sat. NaCl, dried over Na2SO4 and concentrated at reduced pressure to produce 1.68 g of the expected product (yield: 86%) used as it is for the next step.

Workup

washThe organic phase is washed with 1N HCl, H2O, sat. NaCl
dry with materialdried over Na2SO4
concentrationconcentrated at reduced pressure

Sources & evidence

ORD record: ord-9e07e00d35cc45cba1a6f7e9b5acf540
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703747B2

Reaction notes

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