N-Methoxy-N-methylbutyramide → HCID 71285237, compound

HRID 1481737Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[CH:5]2.[Li]CCCC.CON(C)[C:30](=[O:34])[CH2:31][CH2:32][CH3:33]>C1COCC1>[Si:15]([O:14][CH2:13][CH2:12][C:6]1[N:7]([CH3:11])[C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([C:30](=[O:34])[CH2:31][CH2:32][CH3:33])=[CH:10][CH:9]=2)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: -78 °C

Procedure

To solution of 5-bromo-2-(2-(tert-butyldimethylsilyloxy)ethyl)-1-methyl-1H-indole (9.963 g, 27.04 mmol) in THF (100 mL) at −78° C. was added solution of n-BuLi (2.5M hexanes, 13.0 mL, 32.50 mmol) dropwise over 10 min. Reaction was stirred at −78° C. for 10 min before solution of N-methoxy-N-methylbutyramide (4.30 g, 32.78 mmol) in THF (10 mL) was added dropwise. Reaction was stirred at −78° C. for 15 min and then quenched with NH4Cl (aqueous saturated, 30 mL). Once ambient temperature was reached in the reaction mixture product was extracted with EtOAc (2×100 mL). Combined organics were washed with NaCl (aqueous saturated) and dried over Na2SO4. Upon solvent removal residue was purified by column chromatography using EtOAc/hexanes (gradient 0-30%) to afford 1-(2-(2-(tert-butyldimethylsilyloxy)ethyl)-1-methyl-1H-indol-5-yl)butan-1-one (6.620 g, 68%) as white solid.

Workup

customReaction
additionwas added dropwise
customReaction
customquenched with NH4Cl (aqueous saturated, 30 mL)
customOnce ambient temperature
extractionwas extracted with EtOAc (2×100 mL)
washCombined organics were washed with NaCl (aqueous saturated)
dry with materialdried over Na2SO4
customUpon solvent removal residue
customwas purified by column chromatography

Sources & evidence

ORD record: ord-ee258a6f126b40be83829f3f3695cee2
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409905B2

Reaction notes

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