Aluminium lithium hydride → 5-[4-(3-Chlorophenyl)-7-ethyl-2-phenylpyrrolo[1,2-b]pyridazin-3-yl]-1-pentanol

HRID 860463Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[C:15]3[N:16]([C:35]([CH2:38][CH3:39])=[CH:36][CH:37]=3)[N:17]=[C:18]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:19]=2[CH2:20][CH2:21][CH2:22][CH2:23][C:24](OCC)=[O:25])[CH:11]=[CH:12][CH:13]=1>O1CCCC1>[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2[C:15]3[N:16]([C:35]([CH2:38][CH3:39])=[CH:36][CH:37]=3)[N:17]=[C:18]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:19]=2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25])[CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of lithium aluminum hydride (98.8 mg) in tetrahydrofuran (10 mL) was added ethyl 5-[4-(3-chlorophenyl)-7-ethyl-2-phenylpyrrolo[1,2-b]pyridazin-3-yl]pentanoate (600 mg) in tetrahydrofuran (10 mL) under ice-water cooling and the mixture was stirred at 0° C. for 2 hours. The reaction was quenched with saturated potassium sodium tartrate solution and the insolubles were filtereed off and washed with ethyl acetate. The filtrates were washed with 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 (10:1–2:1) to give 5-[4-(3-chlorophenyl)-7-ethyl-2-phenylpyrrolo[1,2-b]pyridazin-3-yl]-1-pentanol as an yellow oil (478 mg).

Workup

customThe reaction was quenched with saturated potassium sodium tartrate solution
washwashed with ethyl acetate
washThe filtrates were washed with brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was purified by silica gel column chromatography
washeluting with a mixture of hexane and ethyl acetate (10:1–2:1)

Sources & evidence

ORD record: ord-5a893188cd9b40c4b8f00aee691db358
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153854B2

Reaction notes

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