HCID 71143714, compound → HCID 71143665, compound

HRID 1506998Notes

Reaction equation

HRID 1506998 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:30])([CH2:24][N:25]1[CH:29]=[N:28][N:27]=[N:26]1)[C:10]([C:13]1[N:18]=[CH:17][C:16](/[CH:19]=[CH:20]\[C:21](=[O:23])[CH3:22])=[CH:15][CH:14]=1)([F:12])[F:11]>CO.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:30])([CH2:24][N:25]1[CH:29]=[N:28][N:27]=[N:26]1)[C:10]([C:13]1[N:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21](=[O:23])[CH3:22])=[CH:15][CH:14]=1)([F:11])[F:12]

Participants

4

Reactant 1

HCID 71143714HCID 71143714, compound

Product 1

HCID 71143665HCID 71143665, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 7 (30 mg, 0.071 mmol) in CH3OH (10 mL) was added 10% Pd/C (10 mg) under N2 atmosphere and the reaction mixture was stirred under hydrogen atmosphere at RT for 30 min. The reaction mixture was filtered through a pad of Celite®, the Celite® bed was washed thoroughly with EtOAc (3×10 mL) and then the filtrate was concentrated under vacuum. The crude material was purified by column chromatography (eluting with EtOAc/hexane) to afford 8 (16 mg, 0.037 mmol, 53%) as a colorless semi-solid. 1H NMR (500 MHz, DMSO-d6): δ 9.11 (s, 1H), 8.45 (s, 1H), 7.74 (d, J=8.0 Hz, 1H), 7.34 (d, J=8.0 Hz, 1H), 7.24-7.21 (m, 2H), 7.17-7.12 (m, 1H), 6.89-6.85 (m, 1H), 5.61 (d, J=14.5 Hz, 1H), 5.06 (d, J=14.5 Hz, 1H), 2.81 (br s, 4H), 2.08 (s, 3H). MS (ESI): m/z 424 [M++1]. HPLC: 95.3%.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. washthe Celite® bed was washed thoroughly with EtOAc (3×10 mL)
  3. concentrationthe filtrate was concentrated under vacuum
  4. customThe crude material was purified by column chromatography (eluting with EtOAc/hexane)

Sources & evidence

ORD record
ord-acd9dad2633245359e927a4608bd1c74
Source dataset
uspto-grants-2015_12
Patent number
US09221791B2

Reaction notes

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