Pyridine → HCID 57800464, compound

HRID 913657Notes

Reaction equation

HRID 913657 reaction equation
[C:1]([C:3]1[C:4]([C:24]([F:27])([F:26])[F:25])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[O:17][C:16]([C:18]([NH2:20])=O)=[CH:15][CH:14]=1)[C:7]([CH2:21][CH2:22][CH3:23])=[CH:6]2)#[N:2].N1C=CC=CC=1.O=P(Cl)(Cl)Cl>C(Cl)Cl>[C:18]([C:16]1[O:17][C:13]([CH2:12][N:8]2[C:9]3[C:5](=[C:4]([C:24]([F:26])([F:27])[F:25])[C:3]([C:1]#[N:2])=[CH:11][CH:10]=3)[CH:6]=[C:7]2[CH2:21][CH2:22][CH3:23])=[CH:14][CH:15]=1)#[N:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 57800435HCID 57800435, compound

Product 1

HCID 57800464HCID 57800464, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution containing 5-{[5-cyano-2-propyl-4-(trifluoromethyl)-1H-indol-1-yl]methyl}-2-furancarboxamide (Example 271B) (0.388 g, 1.03 mmol), pyridine (10 mL) and CH2Cl2 (25 mL) was cooled to 0-5° C. This mixture was mixed with POCl3 (0.792 g, 5.17 mmol) and the resulting mixture was stirred at rt for 2 h. The reaction mixture was then partitioned between CH2Cl2 and saturated NaHCO3. The organics were washed with 1.0N HCl, dried (MgSO4) and concentrated to dryness. The residue was purified by flash chromatography (0-10% EtOAc-hexanes gradient) to afford a pure product (0.204 g, 55% yield): MS (ES) m/z 357 (M+).

Workup

  1. customThe reaction mixture was then partitioned between CH2Cl2 and saturated NaHCO3
  2. washThe organics were washed with 1.0N HCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by flash chromatography (0-10% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-75da4838d14e4a8e8838137c16ea092e
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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