Potassium Carbonate → HCID 68471130, compound

HRID 506788Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[Cl:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]2[N:21]([S:40]([C:43]3[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=3)(=[O:42])=[O:41])[C:22]([C:24]3[C:28]4=[N:29][C:30]([O:35][CH3:36])=[C:31]([O:33][CH3:34])[CH:32]=[C:27]4[N:26]([CH2:37][CH2:38]I)[CH:25]=3)=[CH:23][C:16]=12>CC#N>[Cl:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]2[N:21]([S:40]([C:43]3[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=3)(=[O:42])=[O:41])[C:22]([C:24]3[C:28]4=[N:29][C:30]([O:35][CH3:36])=[C:31]([O:33][CH3:34])[CH:32]=[C:27]4[N:26]([CH2:37][CH2:38][N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)[CH:25]=3)=[CH:23][C:16]=12

Participants

Conditions

Temperature: 60 °C

Procedure

Add 1-methylpiperazine (3.5 equiv., 35.2 mg, 39.1 μmol, 0.352 mmol) and K2CO3 (13.8 mg, 0.10 mmol) to bisazaindole 32 (64 mg, 0.10 mmol) in CH3CN (6.0 mL). After heating at 60° C. for 48 h, the reaction medium is concentrated under vacuum and the residue of raw product is submitted to flash chromatography on SiO2 (MeOH at 2-4%/CH2Cl2/heptane) to give 35 (40 mg, 64.3%) as a white solid: 1H NMR (CDCl3) δ 8.23 (d, 1H, J=5.4 Hz), 7.68 (d, 2H, J=8.1 Hz), 7.61 (s, 1H), 7.10 (m, 5H), 4.25 (t, 2H, J=6.6 Hz), 4.01 (s, 3H), 3.97 (s, 3H), 2.83 (t, 2H, J=6.9 Hz), 2.57-2.46 (m broad, 8H), 2.28 (s, 3H), TLC (MeOH at 10%/CH2Cl2, 0.25% of NH3) Rf=0.45, m/z obs.=609.04 (M+1).

Workup

concentrationthe reaction medium is concentrated under vacuum

Sources & evidence

ORD record: ord-b833c6eb1a0441779a7462083ee632a0
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786114B2

Reaction notes

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