Sodium Carbonate → 3-bromo-7-(6-morpholinopyridin-3-yl)-9H-carbazole-1-carboxamide

HRID 2410921Notes

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.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[CH:29][C:30]([N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[N:31][CH:32]=2)O1.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:27]1[CH:32]=[N:31][C:30]([N:33]2[CH2:34][CH2:35][O:36][CH2:37][CH2:38]2)=[CH:29][CH:28]=1)[CH:8]=3

Participants

Conditions

Temperature: 105 °C

Procedure

3-Bromo-7-iodo-9H-carbazole-1-carboxamide 481A (100 mg, 0.241 mmol), 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine (84 mg, 0.289 mmol), PdCl2(dppf)-CH2Cl2 adduct (39.4 mg, 0.048 mmol), and Na2CO3 (2M) (0.602 mL, 1.205 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 450.97 (M+H)+.

Workup

customThe mixture was flushed with N2

Sources & evidence

ORD record: ord-e0334d5668754c9e9056aa97f1d115dd
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

Loading…