Pyridine, hydrofluoride (1:1) → HCID 68814399, compound

HRID 1436684Notes

Reaction equation

HRID 1436684 reaction equation
[F:1][B-](F)(F)F.N#[O+].N1C=CC=CC=1.[FH:14].[CH3:15][O:16][C:17](=[O:43])[C:18]1[CH:30]=[C:29]([C:31]2([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)SCCCS2)[CH:28]=[C:20]([C:21]([N:23]([CH3:27])[CH2:24][CH2:25][CH3:26])=[O:22])[CH:19]=1>ClCCl>[CH3:15][O:16][C:17](=[O:43])[C:18]1[CH:30]=[C:29]([C:31]([F:1])([F:14])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:28]=[C:20]([C:21]([N:23]([CH3:27])[CH2:24][CH2:25][CH3:26])=[O:22])[CH:19]=1

Participants

5

Reactant 3

HCID 64774Pyridine, hydrofluoride (1:1)HCID 11137142Nitrilooxonium tetrafluoroborateHCID 86615014HCID 86615014, compound

Product 1

HCID 68814399HCID 68814399, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Chill a solution of nitrosonium tetrafluoroborate (0.074 g, 0.63 mmol), hydrogen fluoride-pyridine (0.250 mL) in dichloromethane (2 mL) in a plastic bottle. Add a solution of N-methyl-5-(2-phenyl-[1,3]dithian-2-yl)-N-propyl-isophthalamic acid methyl ester (0.123 g, 0.286 mmol) in dichloromethane (1 mL) to the bottle and stir at room temperature for 2 h. Dilute the solution with dichloromethane (5 mL) and filter though a pad of magnesium sulfate and aluminum oxide. Wash solid with ethyl acetate (50 mL), concentrate and purify (silica gel chromatography, eluting with 20:80 to 30:70 ethyl acetate:hexanes) to give the title compound (42%).

Workup

  1. filtrationfilter though a pad of magnesium sulfate and aluminum oxide
  2. washWash solid with ethyl acetate (50 mL)
  3. concentrationconcentrate
  4. custompurify
  5. wash(silica gel chromatography, eluting with 20:80 to 30:70 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-190cf4026f6a456dbbdf9d7505324a12
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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