Triphenylphosphine → 2-nitro-N-[2-(7-oxo-7H-furo[2,3-c]pyridin-6-yl)ethyl]-N-[3-(tetrahydropyran-2-yloxy)propyl]benzenesulfonamide

HRID 1183080Notes

Reaction equation

HRID 1183080 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OC(C)(C)C)=O)=O)(C)(C)C.O[CH2:37][CH2:38][N:39]1[CH:44]=[CH:43][C:42]2[CH:45]=[CH:46][O:47][C:41]=2[C:40]1=[O:48].[N+:49]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=1[S:58]([NH:61][CH2:62][CH2:63][CH2:64][O:65][CH:66]1[CH2:71][CH2:70][CH2:69][CH2:68][O:67]1)(=[O:60])=[O:59])([O-:51])=[O:50]>O1CCCC1>[N+:49]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=1[S:58]([N:61]([CH2:37][CH2:38][N:39]1[CH:44]=[CH:43][C:42]2[CH:45]=[CH:46][O:47][C:41]=2[C:40]1=[O:48])[CH2:62][CH2:63][CH2:64][O:65][CH:66]1[CH2:71][CH2:70][CH2:69][CH2:68][O:67]1)(=[O:59])=[O:60])([O-:51])=[O:50]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 686733412-nitro-N-[3-(tetrahydropyran-2-yloxy)propyl]benzenesulfonamideHCID 686744936-(2-hydroxyethyl)-6H-furo[2,3-c]pyridin-7-one

Product 1

HCID 686751362-nitro-N-[2-(7-oxo-7H-furo[2,3-c]pyridin-6-yl)ethyl]-N-[3-(tetrahydropyran-2-yloxy)propyl]benzenesulfonamideYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (393 mg, 1.5 mmol) and azodicarboxylic acid di-tert-butyl ester (345 mg, 1.5 mmol) were added to a tetrahydrofuran (THF) solution (10 ml) of 6-(2-hydroxyethyl)-6H-furo[2,3-c]pyridin-7-one (179 mg, 1.0 mmol) and 2-nitro-N-[3-(tetrahydropyran-2-yloxy)propyl]benzenesulfonamide (413 mg, 1.2 mmol), and stirred overnight. The resulting reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→0:1). The purified product was concentrated to dryness under reduced pressure to thereby obtain 286 mg (yield: 57%) of 2-nitro-N-[2-(7-oxo-7H-furo[2,3-c]pyridin-6-yl)ethyl]-N-[3-(tetrahydropyran-2-yloxy)propyl]benzenesulfonamide as a white amorphous solid.

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1→0:1)
  4. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9b77d55d938d4c40a6368495b126f7b9
Source dataset
uspto-grants-2014_03
Patent number
US08664217B2

Reaction notes

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