HCID 21949856, compound → HCID 21949766, compound

HRID 558288Notes

Reaction equation

HRID 558288 reaction equation
C([O:8][CH2:9][CH2:10][C:11]1[NH:15][N:14]=[C:13]([CH2:16][CH3:17])[C:12]=1[O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([F:27])[CH:26]=1)[C:22]#[N:23])C1C=CC=CC=1>ClCCl.[Fe](Cl)(Cl)Cl>[CH2:16]([C:13]1[C:12]([O:18][C:19]2[CH:20]=[C:21]([CH:24]=[C:25]([F:27])[CH:26]=2)[C:22]#[N:23])=[C:11]([CH2:10][CH2:9][OH:8])[NH:15][N:14]=1)[CH3:17]

Participants

4

Reactant 1

HCID 21949856HCID 21949856, compound

Product 1

HCID 21949766HCID 21949766, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6344DichloromethaneSolvent2×

Procedure

Iron(III)chloride (9.30 g, 57.5 mmol) was added to a solution of the pyrazole from Example 147 (2.10 g, 5.75 mmol) in dichloromethane (90 ml) under nitrogen at room temperature. After stirring for 20 minutes the mixture was diluted with dichloromethane (50 ml), washed with water (100 ml) then saturated aqueous sodium ethylenediaminetetraacetate solution (70 ml), dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (98:2 changing to 95:5, by volume) to provide the title compound (1.2 g) as a brown oil which solidified on standing.

Workup

  1. washwashed with water (100 ml)
  2. dry with materialsaturated aqueous sodium ethylenediaminetetraacetate solution (70 ml), dried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (98:2 changing to 95:5, by volume)

Sources & evidence

ORD record
ord-51c11ff1459a48c38555dc6e1a400eb9
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

Loading…