Triphenylphosphine → HCID 22388036, compound

HRID 1699950Notes

Reaction equation

HRID 1699950 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([OH:23])[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:18].[S:24]1[CH:28]=[CH:27][C:26]([CH2:29]O)=[CH:25]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>ClCCl.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:22]=[C:21]([O:23][CH2:29][C:26]2[CH:27]=[CH:28][S:24][CH:25]=2)[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:13]=[C:8]2[N:7]=[C:6]1[CH3:18]

Participants

7

Reactant 4

HCID 11776Triphenylphosphine2×HCID 123570Thiophene-3-methanol2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 22388051HCID 22388051, compound

Product 1

HCID 22388036HCID 22388036, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of methyl 3-[2-chloro-4-hydroxybenzyl]-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (240 mg), 3-thiophenemethanol (68 mg) and triphenylphosphine (218 mg) in dry dichloromethane were added to diethyl azodicarboxylate (139 mg) under ice-cooling. After 2 hr, the reaction mixture was stirred at room temperature. After 6 hr, to a suspension of 3-thiophenemethanol (34 mg) and triphenylphosphine (109 mg) in dry dichloromethane was added diethyl azodicarboxylate (69 mg) under ice-cooling. After 20 hr, the reaction mixture was subjected to flash silica gel chromatography (silica gel 60 ml, eluent: chloroform). The eluate was recrystallized from ethyl acetate to give the objective compound (143 mg) as colorless crystals.

Workup

  1. temperaturecooling
  2. waitAfter 6 hr
  3. temperaturecooling
  4. waitAfter 20 hr
  5. customThe eluate was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f9bbd2db63d7472b9d50d9dd1f401c4c
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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