Sodium Carbonate → 7-Amino-3-m-tolyl-9H-carbazole-1-carboxamide

HRID 2410917Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

7-Amino-3-bromo-9H-carbazole-1-carboxamide 470B (350 mg, 1.151 mmol), m-tolylboronic acid (313 mg, 2.302 mmol), PdCl2(dppf)-CH2Cl2 adduct (94 mg, 0.115 mmol), and Na2CO3 (2M) (2.88 mL, 5.75 mmol) were mixed with DME (15 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 316.04 (M+H)+. 1H NMR (DMSO-d6) δ ppm 10.89 (s, 1H), 8.30 (s, 1H), 8.23 (s, 1H), 8.03 (s, 1H), 7.82 (d, 1H, J=8.2), 7.67 (s, 1H), 7.63 (d, 1H, J=7.6), 7.41(s, 1H), 7.36 (t, 1H, J=7.6), 7.14 (d, 1H, J=7.6), 6.81 (s, 1H), 6.5 (d, 1H, J=8.3), 5.24 (bs, 2H), 2.42 (s, 3H).

Workup

customThe mixture was flushed with N2
customThe mixture was purified

Sources & evidence

ORD record: ord-289acf1d531c4221a53f7f82c9cc407c
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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