Triethylamine → HCID 86597473, compound

HRID 2250601Notes

Reaction equation

HRID 2250601 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, compoundYield 67.9%

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 yellow 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-cf0e55fcd5314a46b417fab9cf8d71c8
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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