Triphenylphosphine → HCID 68517704, compound

HRID 1716297Notes

Reaction equation

HRID 1716297 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C[CH:21]([O:23]C(/N=N/C(OC(C)C)=O)=O)C.Br[C:35]1[C:40]([CH:41](O)[CH3:42])=[CH:39][CH:38]=[CH:37][N:36]=1.[C:44]1([CH3:62])[CH:49]=[CH:48][C:47]([O:50][C:51]2[CH:56]=[CH:55][C:54]([NH:57][S:58]([CH3:61])(=[O:60])=[O:59])=[CH:53][CH:52]=2)=[CH:46][CH:45]=1>C1COCC1>[CH3:21][O:23][C:35]1[C:40]([CH:41]([N:57]([C:54]2[CH:55]=[CH:56][C:51]([O:50][C:47]3[CH:46]=[CH:45][C:44]([CH3:62])=[CH:49][CH:48]=3)=[CH:52][CH:53]=2)[S:58]([CH3:61])(=[O:60])=[O:59])[CH3:42])=[CH:39][CH:38]=[CH:37][N:36]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 3858049N-[4-(4-methylphenoxy)phenyl]methanesulfonamideHCID 5363146Diisopropyl azodicarboxylateHCID 104428211-(2-bromopyridin-3-yl)ethanol

Product 1

HCID 68517704HCID 68517704, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of PPh3 (0.26 g, 1.0 mmol) and DIAD (0.2 mL, 1.0 mmol) in dry THF (3 mL) at 0 C was added a solution of 1-(2-bromo-pyridin-3-yl)-ethanol (0.14 g, 0.67 mmol) from Step A and N-(4-p-tolyloxy-phenyl)-methanesulfonamide (0.19 g, 0.7 mmol) from Example 42 step B in dry THF (2 mL). After 1 h, the reaction was warmed to room temperature and stirred for 3 h. The reaction was then concentrated under the reduced pressure. The residue was diluted with EtOAc and the precipitates were filtered. The filtrate was brought to the usual work-up. The crude material was purified by chromatography (silica gel, 30% EtOAc/hexanes) to give the desired product. MS (EI) 413 (M+H)+.

Workup

  1. concentrationThe reaction was then concentrated under the reduced pressure
  2. additionThe residue was diluted with EtOAc
  3. filtrationthe precipitates were filtered
  4. customThe crude material was purified by chromatography (silica gel, 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f7074836c98143328112d602a17a8724
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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