Indole → N-(4-methylphenyl)indole

HRID 227862

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1.CC([O-])(C)C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2OC)CCCCC1.C1(C)C=CC=CC=1>[CH3:17][C:14]1[CH:15]=[CH:16][C:11]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

An oven-dried test tube was purged with argon and then charged with 2-dicyclohexylphosphino-2′-methoxy-1,1′-biphenyl (14.5 mg, 0.038 mmol, 7.5 mol %) and Pd2(dba)3 (11.6 mg, 0.013 mmol, 5.0 mol % Pd). Toluene (1.0 mL), indole (71 mg, 0.61 mmol), 4-chlorotoluene (60 mL, 0.51 mmol), and NaOt-Bu (70 mg, 0.73 mmol) were then added. The tube was fitted with a septum, purged with argon and heated at 100° C. for 28 h. The reaction was then cooled to room temperature, diluted with ether (20 mL), filtered through Celite and concentrated in vacuo. The residue was purified by flash chromatography on silica gel to afford 99 mg (94%) of a colorless oil.

Workup

customAn oven-dried test tube was purged with argon
customThe tube was fitted with a septum
custompurged with argon
temperatureThe reaction was then cooled to room temperature
additiondiluted with ether (20 mL)
filtrationfiltered through Celite
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-d9fb925b05a9485aa7060f8cf483127b
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560582B2

Linked notes

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