Triethylamine → HCID 86597473, compound

HRID 860457Notes

Reaction equation

HRID 860457 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[N:10]([CH:17]=[CH:18][CH:19]=3)[N:11]=[C:12]([CH3:16])[C:13]=2[CH2:14][OH:15])=[CH:4][CH:3]=1.C(N(CC)CC)C>ClCCl.CS(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]3[N:10]([CH:17]=[CH:18][CH:19]=3)[N:11]=[C:12]([CH3:16])[C:13]=2[CH:14]=[O:15])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 68804032HCID 68804032, compound

Product 1

HCID 86597473HCID 86597473, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(4-fluorophenyl)-2-methylpyrrolo-[1,2-b]pyridazin-3-yl]methanol (505 mg) and triethylamine (997 mg) in dichloromethane (4 mL) and dimethyl sulfoxide (2 mL) was added sulfur trioxide pyridine complex (941 mg) in an ice-water bath under nitrogen. After 30 minutes, the mixture was stirred at ambient temperature for 2 hours. The reaction mixture was concentrated to about ⅓ volume. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with water three times and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by flash silica gel chromatography (silica gel, 30 mL) eluted with hexane-chloroform=3-1 and 2-1 to give 4-(4-fluorophenyl)-2-methylpyrrolo[1,2-b]pyridazine-3-carbaldehyde as an yelow solid (340 mg, 67.9%).

Workup

  1. concentrationThe reaction mixture was concentrated to about ⅓ volume
  2. customThe mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water three times and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by flash silica gel chromatography (silica gel, 30 mL)
  7. washeluted with hexane-chloroform=3-1 and 2-1

Sources & evidence

ORD record
ord-72dce69ecc8a419bb869f20cf6811785
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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