Dimethylamine → 3-(2-(1H-indol-3-yl)-2-oxoethyl)-1-(3-azidopropyl)-3-hydroxy-5-methylindolin-2-one

HRID 1523072Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=[O:12])[CH3:11])=[CH:2]1.[N:13]([CH2:16][CH2:17][CH2:18][N:19]1[C:27]2[C:22](=[CH:23][C:24]([CH3:28])=[CH:25][CH:26]=2)[C:21](=[O:29])[C:20]1=[O:30])=[N+:14]=[N-:15].CNC>CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=[O:12])[CH2:11][C:21]2([OH:29])[C:22]3[C:27](=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=3)[N:19]([CH2:18][CH2:17][CH2:16][N:13]=[N+:14]=[N-:15])[C:20]2=[O:30])=[CH:2]1

Participants

Conditions

Temperature: 130 °C

Procedure

To a clean Biotage microwave vial was added 1-(1H-indol-3-yl)ethanone (0.023 grams, 0.143 mmol, purchased from Fisher Scientific), 1-(3-azidopropyl)-5-methylindoline-2,3-dione (0.02 grams, 0.082 mmol) and 0.27 mL of methanol. After the addition of 9.0 μL of dimethyl amine (40% by weight solution in water, purchased from Fisher Scientific), the vial was sealed and heated in a Biotage Initiator for ten minutes at 130° C. It was then concentrated and purified using a Teledyne ISCO hexanes/ethyl acetate gradient on silica gel. A subsequent purification was done using a preparative thin layer chromatography (ethyl acetate, hexanes (2:1)). Yield 14%. 1H-NMR δ 8.87 (bs, 1H), 8.34 (m, 1H), 7.76 (s, 1H), 7.40 (m, 1H), 7.29 (m, 3H), 7.10 (d, 1H), 6.77 (d, 1H), 5.0 (bs, OH), 3.77 (m, 2H), 3.60 (d, 1H), 3.41 (t, 2H), 3.34 (d, 1H), 2.27 (s, 3H), 1.96 (m, 2H).

Workup

customthe vial was sealed
concentrationIt was then concentrated
custompurified
customA subsequent purification

Sources & evidence

ORD record: ord-8e1d3c418e784e2db91d354b8c5a57b7
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079853B2

Reaction notes

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