Aluminum(III) Chloride → HCID 11954403, compound

HRID 1805865Notes

Reaction equation

C([N:8]1[C:16]2[C:15]([O:17][C:18]3[C:25]([CH3:26])=[CH:24][C:21]([C:22]#[N:23])=[CH:20][C:19]=3[CH3:27])=[N:14][C:13]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][CH:30]=3)=[N:12][C:11]=2[CH:10]=[CH:9]1)C1C=CC=CC=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClC1C=CC=CC=1Cl>[C:35]([C:32]1[CH:33]=[CH:34][C:29]([NH:28][C:13]2[N:14]=[C:15]([O:17][C:18]3[C:19]([CH3:27])=[CH:20][C:21]([C:22]#[N:23])=[CH:24][C:25]=3[CH3:26])[C:16]3[NH:8][CH:9]=[CH:10][C:11]=3[N:12]=2)=[CH:30][CH:31]=1)#[N:36]

Participants

Conditions

Temperature: 160 °C

Procedure

To a suspension of 4-(5-benzyl-2-(4-cyanophenylamino)-5H-pyrrolo[3,2-d]pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile (240 mg, 0.51 mmol) in 1,2-dichlorobenzene (20 mL) was added AlCl3 (681 mg, 5.1 mmol). The reaction mixture was heated at 160° C. for 1.5 h, during which time the reaction mixture became dark and homogeneous. Upon completion of the reaction, the reaction mixture was cooled and washed with NH4Cl. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by preparative TLC TLC eluting with Hexanes:Ethyl acetate (2.5:1) and produced the product as a pink solid (51 mg, 26%).

Workup

customUpon completion of the reaction
temperaturethe reaction mixture was cooled
washwashed with NH4Cl
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified by preparative TLC TLC
washeluting with Hexanes:Ethyl acetate (2.5:1)

Sources & evidence

ORD record: ord-634e3ec2c614415a98ea28c50cc3d3df
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354532B2

Reaction notes

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