Toluene → tert-butyl 4-(6-bromo-8-carbamoyl-9H-carbazol-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 2410923Notes

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[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH:28]=2)O1.C([O-])([O-])=O.[Na+].[Na+].C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO>[Br:1][C:2]1[CH:14]=[C:13]2[C:5](=[C:4]([C:16](=[O:17])[NH2:18])[CH:3]=1)[NH:6][C:7]1[CH:8]=[C:9]([C:27]3[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH:28]=3)[CH:10]=[CH:11][C:12]2=1

Participants

Conditions

Temperature: 105 °C

Procedure

3-Bromo-7-iodo-9H-carbazole-1-carboxamide 481A (200 mg, 0.482 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (194 mg, 0.626 mmol), Pd(Ph3P)4 (35 mg, 0.030 mmol), and Na2CO3 (2M) (0.964 mL, 1.928 mmol) were mixed with toluene (10 mL) and MeOH (5 mL) in a sealed microwave vial. The mixture was flushed with N2 and heated at 105° C. in an oil bath for 4 hrs. The mixture was used as it is. MS (ESI) m/z 468.22 (M−H)−.

Workup

customThe mixture was flushed with N2

Sources & evidence

ORD record: ord-26f54b720ef544709feaa832577e9866
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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