5-Bromo-1-methyl-1H-indole → HCID 71284599, compound

HRID 1481695Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[CH:5]2.[Li]CCCC.CON(C)[C:20](=[O:24])[CH2:21][CH2:22][CH3:23]>C1COCC1>[CH3:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([C:20](=[O:24])[CH2:21][CH2:22][CH3:23])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 5-bromo-1-methyl-1H-indole (9.8 g, 46.7 mmol) in THF (40 mL) was added n-BuLi (2.5M in hexanes, 22.3 mL, 55.8 mmol, 1.2 eq) at −78° C. dropwise over 15 min. The mixture was stirred for 30 min at −78° C. before a solution of N-methoxy-N-methylbutyramide (7.35 g, 56.0 mmol, 1.2 eq) in THF (10 mL) was added. After stirred at −78° C. for 10 min, the reaction was quenched with saturated aqueous NH4Cl. The resulting mixture was extracted by ether (3×30 mL) and combined organic layers were dried over Na2SO4. The crude product was purified by flash chromatography (0-10% EtOAc in hexanes) to give the title compound (5.40 g, 26.8 mmol, 57%) as a white solid.

Workup

additionwas added
customthe reaction was quenched with saturated aqueous NH4Cl
extractionThe resulting mixture was extracted by ether (3×30 mL)
dry with materialwere dried over Na2SO4
customThe crude product was purified by flash chromatography (0-10% EtOAc in hexanes)

Sources & evidence

ORD record: ord-6e234d808cd8439983f860554ca8527f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409905B2

Reaction notes

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