HCID 53237706, compound → HCID 53237707, compound

HRID 640705Notes

Reaction equation

HRID 640705 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[C:11]4[CH:19]=[CH:18][O:17][C:16](=[O:20])[C:12]4=[N:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1>CO.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[C:11]4[CH2:19][CH2:18][O:17][C:16](=[O:20])[C:12]4=[N:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 53237706HCID 53237706, compound

Product 1

HCID 53237707HCID 53237707, compoundYield 926.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 7-(4-fluorobenzyl)pyrano[3,4-b]pyrrolo[3,2-d]pyridin-4(7H)-one (0.30 g, 0.102 mmol) and Pd/C (5% Pd, 50 mg) in methanol (100 mL) was shaken in a Parr shaker under hydrogen (20 psi) for 16 hours. The catalyst was filtered off, the filtrate was concentrated and dried in vacuum to provided the title compound as a solid (0.28 g, 4% yield). that was used without further purification in the next step 1H NMR (MeOD) δ; 8.77 (s, 1H), 7.76 (d, 1H, J=3.0 Hz), 7.28 (d, 2H, J=5.1 Hz), 7.07 (d, 2H, J=5.1 Hz), 6.86 (d, 1H, J=3.0 Hz), 4.66 (d, 2H, J=6 Hz), 7,28 (d, 2H, J=6 Hz). MS (APCl, M+H+): 297.1.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customdried in vacuum

Sources & evidence

ORD record
ord-2beaf3218ccb429bacef09d0523de843
Source dataset
uspto-grants-2010_04
Patent number
US07692014B2

Reaction notes

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