Triethylamine → 5-(1,2-Dioxo-4-methyl-3-cyclobuten-3-yl)aminomethyl-3-(3-methanesulfonyloxypropyl)indole

HRID 1769632Notes

Reaction equation

[O:1]=[C:2]1[C:5]([CH3:6])=[C:4]([NH:7][CH2:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[C:12]3[CH2:18][CH2:19][CH2:20][OH:21])[C:3]1=[O:22].C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>ClCCl.C1COCC1>[O:1]=[C:2]1[C:5]([CH3:6])=[C:4]([NH:7][CH2:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][CH:13]=[C:12]3[CH2:18][CH2:19][CH2:20][O:21][S:31]([CH3:30])(=[O:33])=[O:32])[C:3]1=[O:22]

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 5-(1,2-dioxo-4-methyl-3-cyclobuten-3-yl)aminomethyl-3-(3-hydroxypropyl)indole (0.48 g, 0.0016 mol) in 45 mL of dichloromethane-THF (4:1) , cooled at -20° C. under Ar, was added triethylamine (0.28 mL, 0.002 mol) followed by methanesulfonyl chloride (0.16 mL, 0.002 mol) . The resulting solution was stirred at -20° C. for 1.5 h and then it was washed (brine), dried (Na2SO4) and evaporated to give a brown gum. This material was chromatographed (SiO2 /ethyl acetate) to give the title compound (0.50 g, 83%) as a beige foam: IR (neat) 3320 (br), 1785, 1727, 1600 (br), 1350 (br) cm-1 ; 1H NMR (DMSO-d6, 200 MHz) δ10.86 (s, 1H), 9.45 (m, 0.5H), 9.21 (m, 0.5H), 7.48 (s, 1H), 7.33 (d, J=8.3 Hz, 1H), 7.17 (s, 1H), 7.03 (d, J=8.3 Hz, 1H), 4.78 (d, J=5.9 Hz, 1.2H), 4.62 (d, J=6.0 Hz, 0.8H), 4.23 (m, 2H), 3.80 (s, 3H), 3.06 (m, 2H), 2.76 (m, 2H), 2.14 (s, 1.2H), 2.05 (s, 1.8H).

Workup

washit was washed (brine)
dry with materialdried (Na2SO4)
customevaporated
customto give a brown gum
customThis material was chromatographed (SiO2 /ethyl acetate)

Sources & evidence

ORD record: ord-2c92af00bbba4b9dac350b17f576e1f9
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05382592

Reaction notes

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