Aluminium lithium hydride → HCID 68817938, compound

HRID 735484Notes

Reaction equation

HRID 735484 reaction equation
[CH2:1]([N:8]1[C:16]([C:17]2[CH:33]=[CH:32][C:20]([O:21][C:22]3[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=3)[C:25](OC)=[O:26])=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11]([C:34]([F:37])([F:36])[F:35])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[CH2:1]([N:8]1[C:16]([C:17]2[CH:33]=[CH:32][C:20]([O:21][C:22]3[CH:23]=[C:24]([CH2:25][OH:26])[CH:29]=[CH:30][CH:31]=3)=[CH:19][CH:18]=2)=[C:15]2[C:10]([C:11]([C:34]([F:36])([F:37])[F:35])=[CH:12][CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67021520HCID 67021520, compound

Product 1

HCID 68817938HCID 68817938, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

This compound was prepared from methyl 3-{4-[2-benzyl-7-(trifluoromethyl)-2H-indazol-3-yl]phenoxy}benzoate (Example 912; 30 mg, 0.060 mmol), which was dissolved in 1.5 ml diethylether and treated with LiAlH4. The reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with water and stirred for 15 minutes. The slurry was filtered and the product extracted with Et2O/NH4Cl (aq, sat). After evaporation of the solvents, the crude material was purified by HPLC using a gradient with an acidic mobile phase on an ACE-C8 column to afford 19.6 mg of analytically pure product.

Workup

  1. customThe reaction mixture was quenched with water
  2. stirringstirred for 15 minutes
  3. filtrationThe slurry was filtered
  4. extractionthe product extracted with Et2O/NH4Cl (aq, sat)
  5. customAfter evaporation of the solvents
  6. customthe crude material was purified by HPLC
  7. customto afford 19.6 mg of analytically pure product

Sources & evidence

ORD record
ord-ef26f92a6f65452f9bdc9827778c8cc6
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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