Sodium Carbonate → 7-(4-methylpiperazin-1-yl)-3-phenyl-9H-carbazole-1-carboxamide

HRID 2410913Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:22]([NH2:24])=[O:23])[C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[C:9]([N:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1)[CH:8]=3.[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=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>[CH3:21][N:18]1[CH2:19][CH2:20][N:15]([C:9]2[CH:8]=[C:7]3[C:12]([C:13]4[CH:14]=[C:2]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[CH:3]=[C:4]([C:22]([NH2:24])=[O:23])[C:5]=4[NH:6]3)=[CH:11][CH:10]=2)[CH2:16][CH2:17]1

Participants

Conditions

Temperature: 105 °C

Procedure

3-Bromo-7-(4-methylpiperazin-1-yl)-9H-carbazole-1-carboxamide (35 mg, 0.090 mmol), phenylboronic acid (22.04 mg, 0.181 mmol), PdCl2(dppf)-CH2Cl2 adduct (7.38 mg, 9.04 μmol), and Na2CO3 (2M) (0.181 mL, 0.362 mmol) were mixed with DME (1 mL) in a sealed microwave vial. The mixture was flushed with N2 and heated at 105° C. in an oil bath for 1.5 hrs. The mixture was concentrated and purified using preparative HPLC to give titled product. MS (ESI) m/z 385.19 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.08 (s, 1H), 8.46 (s, 1H), 8.29 (s, 1H), 8.15 (s, 1H), 8.02 (d, 1H, J=8.5), 7.87 (d, 2H, J=7.4), 7.50(m, 3H), 7.34 (t, 1H, J=7.3), 7.23 (s, 1H), 6.92 (dd, 1H, J=8.8, 2.1), 3.25-3.15 (m, 8H), 2.25 (s, 3H).

Workup

customThe mixture was flushed with N2
concentrationThe mixture was concentrated
custompurified

Sources & evidence

ORD record: ord-f6751574b32a4f9e8308b5f97602708e
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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