Isopropanol → HCID 68943292, compound

HRID 2377142Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH2:11][CH3:12])[CH:3]=1.C([Li])CCC.CON(C)[C:21]([C:23]1[CH:31]=[C:30]2[C:26]([CH:27]=[CH:28][NH:29]2)=[CH:25][CH:24]=1)=[O:22].C(O)(C)C>C1COCC1.O>[CH2:11]([O:10][C:4]1[CH:3]=[C:2]([C:21]([C:23]2[CH:31]=[C:30]3[C:26]([CH:27]=[CH:28][NH:29]3)=[CH:25][CH:24]=2)=[O:22])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9])[CH3:12]

Participants

Conditions

Temperature: -78 °C

Procedure

A stirred mixture of 4-bromo-2-ethoxy-1-methoxy-benzene (6.52 g, 23.7 mmol) and anhydrous THF (20 mL) was cooled to −78° C., evacuated and refilled with nitrogen for 10 cycles. To this clear solution was slowly added n-butyllithium (9.5 mL, 23.7 mmol) and stirred for 20 min. Then a mixture of 1H-indole-6-carboxylic acid methoxy-methyl-amide (2.20 g, 10.8 mmol) in anhydrous THF (25 mL) was added and stirred for 1 hour at −78° C. The mixture was quenched with isopropanol (4.9 mL, 65 mmol) and water (15 mL). The mixture was extracted with EtOAc (3×50 mL). The combined organic phases were washed with water (2×50 mL), dried over MgSO4 and concentrated to give an oil, which was purified by flash column chromatography (EtOAc, Hexane) to give (3-ethoxy-4-methoxy-phenyl)-(1H-indol-6-yl)-methanone as an oil (2.30 g). The product was used in the next step without further purification.

Workup

customevacuated
additionrefilled with nitrogen for 10 cycles
additionwas added
stirringstirred for 1 hour at −78° C
extractionThe mixture was extracted with EtOAc (3×50 mL)
washThe combined organic phases were washed with water (2×50 mL)
dry with materialdried over MgSO4
concentrationconcentrated
customto give an oil, which
customwas purified by flash column chromatography (EtOAc, Hexane)

Sources & evidence

ORD record: ord-068e6f6d44a94feeb5697365fb6ae0a3
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468446B2

Reaction notes

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