Methoxymethyl-triphenylphosphonium chloride → HCID 69423758, compound

HRID 456923Notes

Reaction equation

HRID 456923 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].C(OC([N:37]1[C:45]2[C:40](=[CH:41][C:42]([CH:46]=O)=[CH:43][CH:44]=2)[CH:39]=[C:38]1[C:48]1[C:49](=[O:58])[NH:50][C:51]2[C:56]([CH:57]=1)=[CH:55][CH:54]=[CH:53][CH:52]=2)=O)(C)(C)C>C1COCC1>[CH3:2][O:3][CH:4]=[CH:46][C:42]1[CH:41]=[C:40]2[C:45](=[CH:44][CH:43]=1)[NH:37][C:38]([C:48]1[C:49](=[O:58])[NH:50][C:51]3[C:56]([CH:57]=1)=[CH:55][CH:54]=[CH:53][CH:52]=3)=[CH:39]2

Participants

5

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 121116895-Formyl-2-(2-oxo-1,2-dihydro-quinolin-3-yl)-indole-1-carboxylic acid tert-butyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 69423758HCID 69423758, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of (methoxymethyl)triphenylphosphonium chloride (3.6 g, 10.5 mmol, 2.1 equiv) and potassium t-butoxide (2.48 g, 22 mmol, 4.4 equiv) was stirred 1 hour at 25° C. before a suspension of t-butyl 5-formyl-2-(2-oxo-1,2-dihydroquinolin-3-yl)-1H-indole-1-carboxylate (5-8, 1.94 g, 5.0 mmol, 1 equiv) in THF (100 mL) was added via canula and the resulting mixture was stirred at 25° C. for 18 hours. The reaction was concentrated and the residue was stirred in saturated NH4Cl solution. The insoluble solid was collected by filtration and sonicated in EtOAc and then water to give 3-{5-[2-methoxyethenyl]-1H-indol-2-yl}quinolin-2(1H)-one (10-1) as a 1:1 mixture of E and Z isomers. MS(M+1)=317.1

Workup

  1. additionwas added via canula
  2. concentrationThe reaction was concentrated
  3. stirringthe residue was stirred in saturated NH4Cl solution
  4. filtrationThe insoluble solid was collected by filtration
  5. customsonicated in EtOAc

Sources & evidence

ORD record
ord-0a2f64524b274db2a37a371c5a1e786b
Source dataset
uspto-grants-2007_03
Patent number
US07186723B2

Reaction notes

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