1,2-Dichloroethane → HCID 68469439, compound

HRID 506784Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:9]([C:11]3[C:15]4=[N:16][C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=[C:14]4[NH:13][CH:12]=3)=[CH:10][C:3]=12.[OH-].[Na+].[Cl:36][CH2:37][CH2:38]Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:36][CH2:37][CH2:38][N:13]1[C:14]2[C:15](=[N:16][C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=2)[C:11]([C:9]2[N:8]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:25])=[O:26])[C:4]3=[N:5][CH:6]=[CH:7][C:2]([Cl:1])=[C:3]3[CH:10]=2)=[CH:12]1

Participants

Conditions

Temperature: 50 °C

Procedure

Heat a mixture of bisazaindole 28 (180 mg, 0.373 mmol), 1,2-dichloroethane (2.0 mL), 9N NaOH (2.0 mL) and tetrabutylammonium bromide (16 mg), with stirring, at 50° C. for 16 h. Then leave the reaction medium to cool to room temperature, extract it with CH2Cl2 (3×), dry (Na2SO4) and concentrate under vacuum. Purification on SiO2 by flash chromatography gives 31 (110 mg, 54%) as a yellow solid: 1H NMR (CDCl3) δ 8.40 (d, 1H, J=5.4 Hz), 7.76 (d, 1H, J=5.2 Hz), 7.70 (d, 2H, J=8.4 Hz), 7.59 (s, 1H), 7.15 (m, 2H), 7.06 (d, 2H, J=8.4 Hz), 7.02 (s, 1H), 4.51 (t, 2H, J=6.4 Hz), 4.06 (s, 3H), 4.00 (s, 3H), 3.90 (t, 2H, J=6.4 Hz), 2.30 (s, 3H), TLC (EtOAc at 40%/heptane) Rf=0.20.

Workup

temperatureHeat
customThen leave
customthe reaction medium
temperatureto cool to room temperature
extractionextract it with CH2Cl2 (3×)
dry with materialdry (Na2SO4)
concentrationconcentrate under vacuum
customPurification on SiO2 by flash chromatography

Sources & evidence

ORD record: ord-4ee1d9db0cbf440aa34fa9b337f9a88c
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786114B2

Reaction notes

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