4-Fluorobenzaldehyde → 4-{3-[1-(4-Fluoro-phenyl)-[1,2,4]triazolo[4,3-a]quinolin-7-ylsulfanyl]-phenyl}-tetrahydro-pyran-4-carbonitrile

HRID 2075690Notes

Reaction equation

HRID 2075690 reaction equation
[NH:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([S:13][C:14]3[CH:15]=[C:16]([C:20]4([C:26]#[N:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH:17]=[CH:18][CH:19]=3)[CH:9]=2)[N:4]=1)[NH2:2].[F:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=O)=[CH:31][CH:30]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(Cl)Cl>[F:28][C:29]1[CH:36]=[CH:35][C:32]([C:33]2[N:4]3[C:5]4[C:10]([CH:11]=[CH:12][C:3]3=[N:1][N:2]=2)=[CH:9][C:8]([S:13][C:14]2[CH:15]=[C:16]([C:20]3([C:26]#[N:27])[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[CH:17]=[CH:18][CH:19]=2)=[CH:7][CH:6]=4)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 12217721Iodo benzene diacetateHCID 582577744-[3-(2-Hydrazino-quinolin-6-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

Product 1

HCID 670909914-{3-[1-(4-Fluoro-phenyl)-[1,2,4]triazolo[4,3-a]quinolin-7-ylsulfanyl]-phenyl}-tetrahydro-pyran-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5i (203 mg, 0.54 mmol) was suspended in CH2Cl2. 4-Fluorobenzaldehyde (0.07 mL, 0.65 mmol) was added, and the reaction was stirred at room temperature for 4 hours. Iodobenzene diacetate (176 mg, 0.54 mmol) was added, and the reaction was stirred overnight at room temperature. The reaction was adsorbed onto silica gel and concentrated, and then purified by silica gel chromatography (20-100% EtOAc in hexanes, followed by 0-10% MeOH in EtOAc) to give the desired product, 5j.

Workup

  1. stirringthe reaction was stirred overnight at room temperature
  2. concentrationconcentrated
  3. custompurified by silica gel chromatography (20-100% EtOAc in hexanes, followed by 0-10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-274852242f36437b9f61aab4c7919ad5
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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