Cesium carbonate → HCID 11586448, compound

HRID 1919661Notes

Reaction equation

HRID 1919661 reaction equation
Br[C:2]1[CH:11]=[N:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.Cl.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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]>[CH:11]1[N:10]=[CH:9][CH:8]=[C:3]2[C:2]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[NH:13][C:4]2=[O:6]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2762700Methyl 3-bromoisonicotinateHCID 164270902-Aminophenylboronic acid hydrochloride

Product 1

HCID 11586448HCID 11586448, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

Methyl 3-bromoisonicotinate (1.0 eq, 1.76 g, 7.65 mmol), 2-aminophenylboronic acid hydrochloride (1.0 eq, 1.33 g, 7.67 mmol) and cesium carbonate (2.0 eq, 4.99 g, 15.31 mmol) were suspended in dioxane (15 ml). The mixture was degassed by bubbling nitrogen for 10 minutes. PdCl2(dppf) (0.05 eq, 280 mg, 0.383 mmol) was added and the mixture was stirred at reflux for 2 hours. The resulting solid was filtered, washed with methanol, water and methanol and dried. Benzo[c][2,6]naphthyridin-5(6H)-one was isolated as an off-white solid (823 mg, 55% yield). LCMS (ES): 95% pure, m/z 197 [M+1]+.

Workup

  1. customThe mixture was degassed
  2. customby bubbling nitrogen for 10 minutes
  3. temperatureat reflux for 2 hours
  4. filtrationThe resulting solid was filtered
  5. washwashed with methanol, water and methanol
  6. customdried

Sources & evidence

ORD record
ord-edd9c31dcbb54f36bad4863a0f8f7861
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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