HCID 22641327, compound → HCID 135804125, compound

HRID 2415500Notes

Reaction equation

HRID 2415500 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:14][C:15]([CH3:19])=[N:16]2)=[CH:11][C:10]=1[F:25])C1C=CC=CC=1>CO.[Pd]>[F:25][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[OH:8])[N:16]=[C:15]([CH3:19])[CH:14]=[C:13]2[N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 1

HCID 22641327HCID 22641327, compound

Product 1

HCID 135804125HCID 135804125, compoundYield 92.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1.5 g (4.46 mmol) of 7-benzyloxy-6-fluoro-2-methyl-4-pyrrolidin-1-yl-quinoline, product of example 99, dissolved in 40 ml of MeOH was treated with 0.375 g of palladium on charcoal (10%) and then hydrogenated at RT for 1.5 h until HPLC analysis indicated the completion of the reaction. The catalyst was filtered off, and the solution was concentrated in vacuo. The residue was triturated with AcOEt, collected by filtration and dried in a high vacuum to give 1.02 g (92.8%) 6-fluoro-2-methyl-4-pyrrolidin-1-yl-quinolin-7-ol as an yellow solid. ISP mass spectrum, m/e: 247.3 (M+1 calculated for C14H15FN2O: 247).

Workup

  1. customthe completion of the reaction
  2. filtrationThe catalyst was filtered off
  3. concentrationthe solution was concentrated in vacuo
  4. customThe residue was triturated with AcOEt
  5. filtrationcollected by filtration
  6. customdried in a high vacuum

Sources & evidence

ORD record
ord-d2b19d5bd2434223b79ab655c31adf03
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

Loading…