Hydride → HCID 68802893, compound

HRID 860444Notes

Reaction equation

[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([CH:25]([CH3:27])[CH3:26])[C:9](/[CH:18]=[CH:19]/[C:20](OCC)=[O:21])=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:5]2=[CH:4][CH:3]=1.[H-]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:6]2[N:7]=[C:8]([CH:25]([CH3:27])[CH3:26])[C:9](/[CH:18]=[CH:19]/[CH2:20][OH:21])=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=3)[C:5]2=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of ethyl(2E)-3-[7-chloro-4-(4-fluorophenyl)-2-isopropylpyrrolo[1,2-b]pyridazin-3-yl]-2-propenoate (50 mg) in toluene was added dropwise 1.5 M diisobutylalminum hydride (0.277 mL) in toluene (24 mL) in a dryice-acetone bath. After addition, the mixture was stirred for 2 hours (−10° C.). The reaction mixture was quenched with sodium, potassium-tartarate and was filtered through Celite. The organic layer was separated, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by flash silica gel chromatography (silica gel, 40 mL) eluted with hexane-ethyl acetate=10-1, 5-1, and 3-1 to give (2E)-3-[7-chloro-4-(4-fluorophenyl)-2-isopropylpyrrolo[1,2-b]pyridazin-3-yl]-2-propen-1-ol as an yellow solid (30 mg).

Workup

additionAfter addition
customThe reaction mixture was quenched with sodium, potassium-tartarate
filtrationwas filtered through Celite
customThe organic layer was separated
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was purified by flash silica gel chromatography (silica gel, 40 mL)
washeluted with hexane-ethyl acetate=10-1, 5-1, and 3-1

Sources & evidence

ORD record: ord-3bdb9943101f4a6e8534983aa48a87ef
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153854B2

Reaction notes

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