Aluminum(III) Chloride → 4-((2-((4-Cyanophenyl)amino)-7h-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)-3,5-dimethylbenzonitrile

HRID 1805845Notes

Reaction equation

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

Participants

Conditions

Temperature: 160 °C

Procedure

To a solution of 4-[7-benzyl-2-(4-cyano-phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy]-3,5-dimethyl-benzonitrile (28 mg, 0.060 mmol) in 1,2-dichlorobenzene (1 mL) was added aluminum chloride (40 mg, 0.30 mmol). The reaction mixture was stirred at 160° C. for 45 min and cooled to room temperature. The mixture was poured into ice water and extracted with CH2Cl2 (2×10 mL). The combined organic solution was washed with brine (10 mL), dried with Na2SO4, and concentrated to dryness. Silica gel chromatography (Hexanes:EtOAc=50:50) yielded 6 mg (27%) of 4-[2-(4-cyano-phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy]-3,5-dimethyl-benzonitrile as a tan solid.

Workup

temperaturecooled to room temperature
extractionextracted with CH2Cl2 (2×10 mL)
washThe combined organic solution was washed with brine (10 mL)
dry with materialdried with Na2SO4
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-c82ccb422b72470fb578ce605decdf78
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354532B2

Reaction notes

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