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2,6-Di-tert-butyl-4-methylpyridine → 4-(3-Chlorophenyl)-7-ethyl-3-(5-methoxypentyl)-2-phenylpyrrolo[1,2-b]pyridazine

HRID 860465
Notes
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Reaction equation

HRID 860465 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[N:10]([C:26]([CH2:29][CH3:30])=[CH:27][CH:28]=3)[N:11]=[C:12]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:13]=2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:5]=[CH:6][CH:7]=1.F[B-](F)(F)F.[CH3:36][O+](C)C.C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[N:10]([C:26]([CH2:29][CH3:30])=[CH:27][CH:28]=3)[N:11]=[C:12]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:13]=2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:36])[CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 693088395-[4-(3-Chlorophenyl)-7-ethyl-2-phenylpyrrolo[1,2-b]pyridazin-3-yl]-1-pentanol

Product 1

HCID 693117044-(3-Chlorophenyl)-7-ethyl-3-(5-methoxypentyl)-2-phenylpyrrolo[1,2-b]pyridazineYield 89.3%

Reagents, catalysts & solvents 1

HCID 11
1,2-Dichloroethane
Solvent

Procedure

A mixture of 5-[4-(3-chlorophenyl)-7-ethyl-2-phenylpyrrolo[1,2-b]pyridazin-3-yl]-1-pentanol (65 mg), trimethyloxonium tetrafluoroborate (275 mg) and 2,6-di-t-butyl-4-methylpyridine (47.8 mg) in 1,2-dichloroethane (3 mL) was stirred at ambient temperature for 4 hours. The solution was washed with water, 1N hydrochloric acid, water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (20:1–5:1) to give 4-(3-chlorophenyl)-7-ethyl-3-(5-methoxypentyl)-2-phenylpyrrolo[1,2-b]pyridazine as an yellow oil (60 mg).

Workup

  1. washThe solution was washed with water, 1N hydrochloric acid, water, saturated sodium bicarbonate solution and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with a mixture of hexane and ethyl acetate (20:1–5:1)

Sources & evidence

ORD record
ord-488bef6e785f45268f44f64befe050f0
Source dataset
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07153854B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes