Sodium Carbonate → 7-(4-benzylpiperazin-1-yl)-3-m-tolyl-9H-carbazole-1-carboxamide

HRID 2410916Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:26]=[C:25]3[C:17]([C:18]4[CH:19]=[C:20](Br)[CH:21]=[C:22]([C:27]([NH2:29])=[O:28])[C:23]=4[NH:24]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31]1([CH3:40])[CH:36]=[CH:35][CH:34]=[C:33](B(O)O)[CH:32]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.COCCOC>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:26]=[C:25]3[C:17]([C:18]4[CH:19]=[C:20]([C:33]5[CH:32]=[C:31]([CH3:40])[CH:36]=[CH:35][CH:34]=5)[CH:21]=[C:22]([C:27]([NH2:29])=[O:28])[C:23]=4[NH:24]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

7-(4-Benzylpiperazin-1-yl)-3-bromo-9H-carbazole-1-carboxamide (100 mg, 0.216 mmol), m-tolylboronic acid (58.7 mg, 0.432 mmol), PdCl2(dppf)-CH2Cl2 adduct (17.62 mg, 0.022 mmol), and Na2CO3 (2M) (0.432 mL, 0.863 mmol) were mixed with DME (4 mL) in a sealed microwave vial. The mixture was flushed with N2 and heated at 100° C. in an oil bath for 4 hrs. The mixture was purified using preparative HPLC to give titled product. MS (ESI) m/z 475.12 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.07 (s, 1H), 8.44 (s, 1H), 8.28 (s, 1H), 8.12 (s, 1H), 8.02 (d, 1H, J=8.6), 7.69 (s, 1H), 7.65 (d, 1H, J=7.0), 7.47(s, 1H), 7.36 (m, 5H), 7.28 (m, 1H), 7.21 (s, 1H), 7.16 (d, 1H, J=7.9), 6.90 (dd, 1H, J=8.5, 2.1), 3.56 (s, 2H), 3.22 (bm, 4H), 2.57 (bm, 4H), 2.42 (s, 3H).

Workup

customThe mixture was flushed with N2
customThe mixture was purified

Sources & evidence

ORD record: ord-0d6fa4c910b9488aa0a89887ae230237
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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