Sodium Carbonate → tert-butyl 4-(8-carbamoyl-6-(4-formyl-3-methylphenyl)-9H-carbazol-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 2410924Notes

Reaction equation

HRID 2410924 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([C:15](=[O:17])[NH2:16])[CH:14]=1)[NH:11][C:10]1[CH:9]=[C:8]([C:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=3)[CH:7]=[CH:6][C:5]2=1.[CH:31]([C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][C:34]=1[CH3:42])=[O:32].C([O-])([O-])=O.[Na+].[Na+]>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>[C:15]([C:13]1[CH:14]=[C:2]([C:36]2[CH:37]=[CH:38][C:33]([CH:31]=[O:32])=[C:34]([CH3:42])[CH:35]=2)[CH:3]=[C:4]2[C:12]=1[NH:11][C:10]1[CH:9]=[C:8]([C:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])[CH2:20][CH:19]=3)[CH:7]=[CH:6][C:5]2=1)(=[O:17])[NH2:16]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 223414664-Formyl-3-methylphenylboronic acidHCID 66604634tert-butyl 4-(6-bromo-8-carbamoyl-9H-carbazol-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 86663075tert-butyl 4-(8-carbamoyl-6-(4-formyl-3-methylphenyl)-9H-carbazol-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To the reaction mixture above (483A) was added 4-formyl-3-methylphenylboronic acid (103 mg, 0.627 mmol), Pd(Ph3P)4 (11.14 mg, 9.64 μmol) and Na2CO3 (0.482 mL, 0.964 mmol). The mixture was stirred at 105 C for 4 hrs. The mixture was filtered and then purified using preparative HPLC to give titled product. MS (ESI) m/z 508.31 (M−H)−.

Workup

  1. filtrationThe mixture was filtered
  2. custompurified

Sources & evidence

ORD record
ord-bab0b9135edd4537a14525a9bb06c82b
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

Loading…