Hydrochloric Acid → HCID 69308932, compound

HRID 860446Notes

Reaction equation

HRID 860446 reaction equation
[H-].[Na+].[Br-].[C:4]([CH2:7][CH2:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:6])=[O:5].[Cl:29][C:30]1[N:34]2[N:35]=[C:36]([CH:48]([CH3:50])[CH3:49])[C:37](C=O)=[C:38]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[C:33]2=[CH:32][CH:31]=1.Cl.[CH3:52]S(C)=O>>[Cl:29][C:30]1[N:34]2[N:35]=[C:36]([CH:48]([CH3:49])[CH3:50])[C:37](/[CH:52]=[CH:9]/[CH2:8][CH2:7][C:4]([OH:6])=[O:5])=[C:38]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[C:33]2=[CH:32][CH:31]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 10717451(3-Carboxypropyl)(triphenyl)phosphanium bromideHCID 86597470HCID 86597470, compound

Product 1

HCID 69308932HCID 69308932, compound

Conditions

Temperature
60 °C

Procedure

To dimethylsulfoxide (0.5 mL) was added 60% sodium hydride in oil (27 mg) and was heated at 60° C. for 40 minutes. To this mixture was added (3-carboxypropyl)(triphenyl)phosphonium bromide (124 mg) at ambient temperature and was stirred for 40 minutes. 7-Chloro-4-(4-fluorophenyl)-2-isopropylpyrrolo[1,2-b]pyridazine-3-carbaldehyde (40 mg) was added therein at ambient temperature. After 4 hours, the reaction mixture was acidified with 1N hydrogen chloride and 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 p-TLC (hexane-ethyl acetate=1-1) to give (4E)-5-[7-chloro-4-(4-fluorophenyl)-2-isopropylpyrrolo[1,2-b]pyridazin-3-yl]-4-pentenoic acid as an yellow oil (21 mg, E:Z=16:1, 56.3%).

Workup

  1. customat ambient temperature
  2. waitAfter 4 hours
  3. customwas partitioned between ethyl acetate and water
  4. washThe organic layer was washed with water three times and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by p-TLC (hexane-ethyl acetate=1-1)

Sources & evidence

ORD record
ord-bc771df6b6734c67a3605885101de3ba
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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