Aluminium lithium hydride → HCID 57825833, compound

HRID 1672155Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([Si](C(C)C)(C(C)C)C(C)C)[N:18]=[CH:17]3)[CH:10]([CH2:33][CH:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][N:18]=[CH:17]3)[CH:10]([CH2:33][CH:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 1-benzyl-3-(tetrahydro-pyran-4-ylmethyl)-4-(1-triisopropylsilanyl-1H-indazol-5-yl)-piperazin-2-one (0.55 g, 1.0 mmol) in 10 mL of THF in a 20 mL microwave vial at 0° C. was slowly added a 1.0 M solution of LiAlH4 (2.1 mL, 2.1 mmol). After gas evolution ceased the vial was capped and heated at 120° C. for 600 seconds in a microwave. The solution was quenched by slow addition to a slurry of NaSO4 decahydrate in THF. The mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo. Purification via flash chromatography afforded 5-[4-benzyl-2-(tetrahydro-pyran-4-ylmethyl)-piperazin-1-yl]-1H-indazole (0.23 g, 59%) as a viscous oil.

Workup

customwas capped
customThe solution was quenched by slow addition to a slurry of NaSO4 decahydrate in THF
filtrationThe mixture was filtered through a pad of celite
concentrationthe filtrate was concentrated in vacuo
customPurification via flash chromatography

Sources & evidence

ORD record: ord-3f0b7e4b59aa42048c24f3cbe591bdb5
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998963B2

Reaction notes

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