Potassium Carbonate → 2-tert-butyl-6-methoxy-3-methyl-1H-indole

HRID 1826221Notes

Reaction equation

Br[C:2]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:3]=1[NH2:4].[CH3:11][C:12]([CH3:17])([C:14]#[C:15][CH3:16])[CH3:13].C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C(=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:12]([C:14]1[NH:4][C:3]2[C:2]([C:15]=1[CH3:16])=[CH:8][CH:7]=[C:6]([O:9][CH3:10])[CH:5]=2)([CH3:17])([CH3:13])[CH3:11]

Participants

Conditions

Temperature: 100 °C

Procedure

2-Bromo-5-methoxyaniline (1.01 g; synthesized according to the process reported by J. H. Tidwell et al., J. Am. Chem. Soc., vol. 116, pp. 11797-11810 (1994)), 2,2-dimethyl-3-pentyne (480 mg; mfd. by Chemsampco), palladium acetate (28.1 mg), tetra-n-butylammonium chloride (1.39 g; mfd. by TOKYO KASEI), potassium carbonate (3.45 g) and triphenylphosphine (65.6 mg) were dissolved in N,N-dimethylacetamide (50 mL). After stirring at 100° C. for 20 hours, the reaction mixture was diluted with water and extracted with ether. The organic layer was washed with a saturated aqueous ammonium chloride solution and water, and then dried. The solvent was distilled off under reduced pressure. The residue was purified twice by silica gel column chromatography (5:1 hexane/ethyl acetate) to yield the title compound (202 mg).

Workup

customsynthesized
extractionextracted with ether
washThe organic layer was washed with a saturated aqueous ammonium chloride solution and water
customdried
distillationThe solvent was distilled off under reduced pressure
customThe residue was purified twice by silica gel column chromatography (5:1 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-d7d0316bf3e14255a10a342643597097
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07049445B2

Reaction notes

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