Propane, 2,2',2''-[methylidynetris(oxy)]tris- → HCID 18187347, compound

HRID 1357654Notes

Reaction equation

HRID 1357654 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[NH:6][C:7]3[N:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]([CH:16]([F:18])[F:17])(C=O)[C:4]=2[CH:3]=1.[CH:21]([O:30][CH:31]([CH3:33])[CH3:32])([O:26][CH:27]([CH3:29])[CH3:28])OC(C)C.CC1C=CC(S(O)(=O)=O)=CC=1.O.CCOC(C)=O.CCCCCC>C(O)(C)C>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[NH:6][C:7]3[N:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]([CH:16]([F:18])[F:17])([CH:21]([O:26][CH:27]([CH3:28])[CH3:29])[O:30][CH:31]([CH3:32])[CH3:33])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 78191Propane, 2,2',2''-[methylidynetris(oxy)]tris-HCID 521998p-Toluenesulfonic acid monohydrateHCID 18187305HCID 18187305, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 18187347HCID 18187347, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Method MMM To a stirred solution of 7-chloro-5-(difluoromethyl)-5-formyl-5,10-dihydrobenzo[b][1,8]naphthyridine (93) (294 mg, 1.0 mmol) in anhydrous triisopropyl orthoformate (8.24 mL, 36.98 mmol) and anhydrous isopropanol (5 mL) at room temperature was added p-TsOH.H2O (380 mg, 2.0 mmol). After 1.5 h at room temperature, the reaction was concentrated in vacuo. Flash chromatography (SiO2, 30% EtOAc-hexane) afforded 94 (132 mg, 34% yield) as a yellow solid.

Workup

  1. concentrationthe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-48c362596fa14ad89eb642cbaba71ed0
Source dataset
uspto-grants-2003_07
Patent number
US06593337B1

Reaction notes

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