2-Methylindole → HCID 21940686, compound

HRID 1883325Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.I[C:12]1[CH:13]=[C:14]([CH3:19])[CH:15]=[C:16]([CH3:18])[CH:17]=1>>[CH3:19][C:14]1[CH:13]=[C:12]([N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:10]=[C:2]2[CH3:1])[CH:17]=[C:16]([CH3:18])[CH:15]=1

Participants

Reactant 2

HCID 72242-Methylindole

HCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 21940686HCID 21940686, compoundYield 95%

Procedure

Using general procedure A, 2-methylindole (165 mg, 1.26 mmol)) was coupled with 5-iodo-m-xylene (150 μL, 1.04 mmol). The crude product was purified by flash chromatography on silica gel (2×15 cm; hexane-ether 40:1; 15 mL fractions). Fractions 4-9 provided 232 mg (95% yield) of the product as a colorless oil. 1H NMR (300 MHz, CDCl3): δ 7.62−7.53 (m, 1H), 7.15−7.05 (m, 4H), 6.98 (s, 2H), 6.39 (s, 1H), 2.41 (s, 6H), 2.31 (d, J=1.0 Hz, 3H).

Workup

customThe crude product was purified by flash chromatography on silica gel (2×15 cm; hexane-ether 40:1; 15 mL fractions)

Sources & evidence

ORD record: ord-fc8f4cafb3de474db86760c437344fcf
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06759554B2

Reaction notes

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