HCID 73053990, compound → HCID 89964666, compound

HRID 1846215Notes

Reaction equation

HRID 1846215 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@:13]2([NH:23][C:24](=[O:34])[C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][N:26]=3)[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[O:16][CH2:15][CH2:14]2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10]>CO.CCOC(C)=O.[Pd]>[NH2:31][C:28]1[CH:29]=[CH:30][C:25]([C:24]([NH:23][C@@:13]2([C:4]3[CH:5]=[CH:6][C:7]([O:8][C:9]([F:12])([F:11])[F:10])=[C:2]([F:1])[CH:3]=3)[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[O:16][CH2:15][CH2:14]2)=[O:34])=[N:26][CH:27]=1

Participants

5

Reactant 1

HCID 73053990HCID 73053990, compound

Product 1

HCID 89964666HCID 89964666, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-N-(4-(3-fluoro-4-(trifluoromethoxy)phenyl)-3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-yl)-5-nitropicolinamide (105 mg, 0.220 mmol, Example 62) in MeOH (1.3 mL) was added a solution of Pd on carbon (0.012 mL, 0.110 mmol) in EtOAc (0.3 mL). The resulting mixture was stirred at room temperature under H2 (balloon) for 2 h. The mixture was filtered through Celite® brand filter agent t and the Celite® brand filter agent was washed with MeOH (2×2 mL). The filtrate was concentrated in vacuo and the residue purified by silica gel column chromatography using ISCO instrument (70-100% EtOAc/hexane) to give the title compound as a yellow solid. MS (ESI, positive ion) m/z: 449.0 (MH+).

Workup

  1. filtrationThe mixture was filtered through Celite® brand
  2. filtrationfilter agent t
  3. filtrationthe Celite® brand filter agent
  4. washwas washed with MeOH (2×2 mL)
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue purified by silica gel column chromatography

Sources & evidence

ORD record
ord-23017d46e2404527bd7e3b05d7895c3a
Source dataset
uspto-grants-2015_02
Patent number
US08952009B2

Reaction notes

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