Sodium Carbonate → 3-bromo-7-(pyridin-3-yl)-9H-carbazole-1-carboxamide

HRID 2410919Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:16]([NH2:18])=[O:17])[C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[C:9](I)[CH:8]=3.[N:19]1[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>[Br:1][C:2]1[CH:3]=[C:4]([C:16]([NH2:18])=[O:17])[C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[C:9]([C:21]1[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=1)[CH:8]=3

Participants

Conditions

Temperature: 105 °C

Procedure

3-Bromo-7-iodo-9H-carbazole-1-carboxamide (100 mg, 0.241 mmol), pyridin-3-ylboronic acid (35.5 mg, 0.289 mmol), PdCl2(dppf)-CH2Cl2 adduct (39.4 mg, 0.048 mmol), and Na2CO3 (2M) (0.482 mL, 0.964 mmol) were mixed with DME (4 mL) in a sealed microwave vial. The mixture was flushed with N2 and heated at 105° C. in an oil bath for 5 hrs. The mixture was used as it is. MS (ESI) m/z 365.88 (M+H)+.

Workup

customThe mixture was flushed with N2

Sources & evidence

ORD record: ord-1bbefaf5eb84483ea4d08aab732849b8
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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