Dimethylamine → HCID 86301276, compound

HRID 1523058Notes

Reaction equation

HRID 1523058 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][C:14]#[CH:15])[C:6](=[O:16])[C:5]2=[O:17].[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([C:27](=[O:29])[CH3:28])=[CH:19]1.CNC>CO>[NH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([C:27](=[O:29])[CH2:28][C:5]2([OH:17])[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([CH3:1])[CH:3]=3)[N:7]([CH2:11][CH2:12][CH2:13][C:14]#[CH:15])[C:6]2=[O:16])=[CH:19]1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 128023-AcetylindoleHCID 90415829HCID 90415829, compound

Product 1

HCID 86301276HCID 86301276, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a clean dry Biotage microwave vial equipped with a stir bar was added the 5-methyl-1-(pent-4-yn-1-yl)indoline-2,3-dione (0.015 grams, 0.066 mmol), 1-(1H-indol-3-yl)ethanone (0.19 grams, 0.12 mmol, purchased from Fisher scientific) and 0.2 mL of methanol. 9.0 μL of dimethyl amine (40% by weight in water) was then added and the solution was placed in a Biotage initiator and heated at 100° C. for thirty minutes. The solution was then concentrated and purified on a Teledyne ISCO using hexanes and ethyl acetate. Yield, 20%. 1H-NMR δ 9.15 (bs, 1H), 8.33 (m, 1H), 7.69 (s, 1H), 7.39 (m, 1H) 7.38 (m, 1H), 7.27 (m, 2H), 7.10 (d, 1H), 6.84 (d, 1H), 5.58 (bs, OH), 3.81 (p, 2H), 3.49 (d, 1H), 3.24 (d, 1H) 2.28 (m, 5H), 2.01 (t, 1H), 1.92 (m, 2H).

Workup

  1. customTo a clean dry Biotage microwave vial equipped with a stir bar
  2. concentrationThe solution was then concentrated
  3. custompurified on a Teledyne ISCO
  4. customYield

Sources & evidence

ORD record
ord-dfd1cdaf85f843a1bc043b2ee57795b8
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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