Nitrogen → tert-Butyl 4-(6-((5-phenyl-5 H-pyrido[3',4':4,5]pyrrolo[2,3-c]pyridin-3-yl)amino)-3-pyridinyl)-1-piperazinecarboxylate

HRID 876044Notes

Reaction equation

HRID 876044 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2Cl)=[CH:6][N:5]=[C:4]([NH:15][C:16]2[N:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[CH:3]=1.CC(C)([O-])C.[Na+].N#N.[NH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C([O-])(=O)C.C([O-])(=O)C.[Pd+2].COCCOC>[C:44]1([N:43]2[C:9]3[CH:10]=[N:11][CH:12]=[CH:13][C:8]=3[C:7]3[CH:6]=[N:5][C:4]([NH:15][C:16]4[N:21]=[CH:20][C:19]([N:22]5[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[CH2:26][CH2:27]5)=[CH:18][CH:17]=4)=[CH:3][C:2]2=3)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 6115AnilineHCID 23676156Sodium t-butoxideHCID 58299708HCID 58299708, compound

Product 1

HCID 58300169tert-Butyl 4-(6-((5-phenyl-5 H-pyrido[3',4':4,5]pyrrolo[2,3-c]pyridin-3-yl)amino)-3-pyridinyl)-1-piperazinecarboxylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

In a 10 mL single-necked round bottom flask were placed tert-butyl 4-(6-(4-chloro-5-(3-chloropyridin-4-yl)pyridin-2-ylamino)pyridin-3-yl)piperazine-1-carboxylate (371) (50 mg, 100 μmol), palladium diacetate (11 mg, 50 μmol), Josiphos (28 mg, 50 μmol), and sodium tert-butoxide (29 mg, 299 μmol). The flask was subjected to 3 cycles of evacuation and back-filling with N2. Aniline (36 μl, 399 μmol) was added under N2 followed by 1,2-dimethoxyethane (3 mL). The resulting mixture was stirred at 100° C. for 20 h. After the volatiles were removed, the residue was subjected to combi-flash column chromatography (methanol/DCM). The product containing compound 372 after concentration was used without further purification. LCMS-ESI (POS), M/Z, M+1: Found 522.2.

Workup

  1. customIn a 10 mL single-necked round bottom flask were placed
  2. customAfter the volatiles were removed
  3. additionThe product containing compound 372
  4. concentrationafter concentration
  5. customwas used without further purification

Sources & evidence

ORD record
ord-31b0d6bf043c48e9963a79a1d8d93f7f
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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