Lithium aluminum hydride → HCID 58204257, compound

HRID 708289Notes

Reaction equation

HRID 708289 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([C:23]#[N:24])[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][C:6]([CH3:25])=[N:5]1)([CH3:3])[CH3:2].[AlH4-].[Li+]>O1CCCC1>[CH:1]([N:4]1[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([CH2:23][NH2:24])[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][C:6]([CH3:25])=[N:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 58204053HCID 58204053, compound

Product 1

HCID 58204257HCID 58204257, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-Isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-8-carbonitrile (0.500 g, 0.00142 mol) in Tetrahydrofuran (14 mL) was added Lithium tetrahydroaluminate (0.00569 mol, 1M in THF, 5.7 mL), dropwise at 0° C. The reaction was stirred for 2 hours and quenched with saturated Na2SO4 until H2 evolution ceased. MgSO4 was added and the whole was diluted with copious amounts of methylene chloride, filtered over celite, and concentrated in vacuo. The crude was purified by flash chromatography (1-15% MeOH in DCM spiked with Et3N) to afford 532 as a yellow solid (238 mg). MS(ESI+) 356.1

Workup

  1. customdropwise at 0° C
  2. customquenched with saturated Na2SO4 until H2 evolution
  3. additionMgSO4 was added
  4. additionthe whole was diluted with copious amounts of methylene chloride
  5. filtrationfiltered over celite
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified by flash chromatography (1-15% MeOH in DCM spiked with Et3N)

Sources & evidence

ORD record
ord-fe1a46437b8748088bb6b2984e58ed9e
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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