HCID 58286938, compound → HCID 58286934, compound

HRID 1962397Notes

Reaction equation

HRID 1962397 reaction equation
C([O:8][C:9]([C:11]1[C:20]2[C:15](=[C:16]([F:21])[CH:17]=[CH:18][CH:19]=2)[C:14](=[O:22])[N:13]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[C:12]=1[CH3:29])=[O:10])C1C=CC=CC=1>CO.[Pd]>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[C:14](=[O:22])[N:13]([C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[C:12]([CH3:29])=[C:11]2[C:9]([OH:10])=[O:8]

Participants

4

Reactant 1

HCID 58286938HCID 58286938, compound

Product 1

HCID 58286934HCID 58286934, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

8-Fluoro-3-methyl-1-oxo-2-pyridin-3-yl-1,2-dihydro-isoquinoline-4-carboxylic acid benzyl ester (0.150 g, 0.386 mmol) was dissolved in methanol (2 mL) and added to 10% Palladium on Charcoal (10 mg). The reaction mixture was stirred under an atmosphere of hydrogen for 60 minutes at room temperature. The reaction mixture was filtered and was rotovaped to give the title compound (0.105 g; yield 91.2%) as a yellow oil. Alternatively, the title acid can be obtained directly under the same conditions according to the above described Pd-catalysed carbonylation in the presence of water instead of benzyl alcohol. LC-MS (m/z) 299.3 (MH+); tR=0.43. 1H NMR (500 MHz, CDCl3): 2.15 (s, 3H), 7.16 (m, 1H), 7.59 (m, 1H), 7.61-7.7 (m, 2H), 7.73 (m, 1H), 8.6 (br. s, 1H), 8.78 (br., 1H).

Workup

  1. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-548f38a25c7e481c8753b205dd2c0c38
Source dataset
uspto-grants-2013_04
Patent number
US08415356B2

Reaction notes

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