Triphenylphosphine → HCID 9925982, compound

HRID 2120254Notes

Reaction equation

HRID 2120254 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:32][CH2:33][CH2:34][C:35]1[CH:43]=[CH:42][CH:41]=[C:40]2[C:36]=1[CH2:37][C:38](=[O:44])[NH:39]2.[Cl:45][C:46]1[CH:47]=[C:48](O)[CH:49]=[N:50][CH:51]=1>O1CCCC1>[Cl:45][C:46]1[CH:47]=[C:48]([O:32][CH2:33][CH2:34][C:35]2[CH:43]=[CH:42][CH:41]=[C:40]3[C:36]=2[CH2:37][C:38](=[O:44])[NH:39]3)[CH:49]=[N:50][CH:51]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5823053-Hydroxy-5-chloropyridineHCID 109430044-(2-Hydroxyethyl)indolin-2-one

Product 1

HCID 9925982HCID 9925982, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (1.74 g, 10 mmol) was added to a solution of triphenylphosphine (2.62 g, 10 mmol) in tetrahydrofuran (20 mL) under nitrogen atmosphere. The mixture was stirred for 15 minutes. To it was then added 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (1.77 g, 10 mmol) followed by 5-chloro-3-pyridinol (1.29 g, 10 mmol). The mixture was stirred at room temperature for 2 days. The precipitate was collected by vacuum filtration, washed with ethyl acetate and dried to give 1.05 g (36%) of 4-[2-(5-chloro-pyridin-3-yloxy)-ethyl]-1,3-dihydro-indol-2-one as a light brown solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 days
  2. filtrationThe precipitate was collected by vacuum filtration
  3. washwashed with ethyl acetate
  4. customdried

Sources & evidence

ORD record
ord-288c5d48cdd243dba0024dc17f17e468
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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