Water → 6-Isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carboxylic acid

HRID 2193017Notes

Reaction equation

HRID 2193017 reaction equation
Br[C:2]1[CH:19]=[CH:18][C:5]2[C:6]([CH:15]([CH3:17])[CH3:16])=[N:7][C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[H+].[B-](F)(F)(F)F.C1CCN2C(=NCCC2)CC1.[OH2:50].[O:51]1[CH2:56]COCC1>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C([CH2-])=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC(O)=O.CC(O)=O.[Pd].[Pd]>[CH:15]([C:6]1[C:5]2[CH:18]=[CH:19][C:2]([C:56]([OH:51])=[O:50])=[CH:3][C:4]=2[C:13]2[C:12](=[O:14])[NH:11][CH:10]=[CH:9][C:8]=2[N:7]=1)([CH3:17])[CH3:16]

Participants

8

Reactant 5

HCID 962WaterHCID 312751,4-DioxaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 593756889-bromo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-oneHCID 86626500tri-(t-butyl)phosphonium HBF4

Product 1

HCID 674172396-Isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carboxylic acid

Reagents, catalysts & solvents 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 11104995trans-Bis(acetato)bis[2-[bis(2-methylphenyl)phosphino]benzyl]dipalladium(II)Catalyst

Conditions

Temperature
100 °C

Procedure

9-bromo-6-isopropylbenzo[c]-1,6-naphthyridin-1(2H)-one (200 mg, 0.631 mmol), molybdenum hexacarbonyl (166 mg, 0.631 mmol), trans-di-mu-acetatobis[2-(di-o-tolylphosphino)benzyl]dipalladium(II) (29.6 mg, 0.0320 mmol), and tri-(t-butyl)phosphonium HBF4 salt (18.3 mg, 0.0630 mmol) were added to a vial, followed by dioxane (2 ml), DBU (0.38 ml, 2.52 mmol) and water (0.114 mL, 6.31 mmol). The resulting suspension was purged with argon (subsurface bubbling) for 5 min, the heated at 100° C. for 18 hr. The reaction mixture was cooled to room temperature, diluted with water (25 mL), and LiOH (45.3 mg) was added. The aqueous layer was washed with ethyl acetate (25 mL). The aqueous layer was acidified with 1 M citric acid (2.5 mL), and the resulting solid was collected by vacuum filtration, then dried under high vacuum at 50° C. for 2 hours to afford 6-isopropyl-1-oxo-1,2-dihydrobenzo[c]-1,6-naphthyridine-9-carboxylic acid. LRMS (ESI) calc'd for (C16H14N2O3) [M+H]+, 283.1; found 283.0.

Workup

  1. customThe resulting suspension was purged with argon (subsurface bubbling) for 5 min
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additiondiluted with water (25 mL), and LiOH (45.3 mg)
  4. additionwas added
  5. washThe aqueous layer was washed with ethyl acetate (25 mL)
  6. filtrationthe resulting solid was collected by vacuum filtration
  7. customdried under high vacuum at 50° C. for 2 hours

Sources & evidence

ORD record
ord-0cd9f1d0bec847e5a55ae2574d9ab864
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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