Aluminium lithium hydride → HCID 67021154, compound

HRID 735488Notes

Reaction equation

HRID 735488 reaction equation
[Cl:1][C:2]1[CH:39]=[CH:38][C:5]([CH2:6][N:7]2[C:15]([C:16]3[CH:33]=[CH:32][C:19]([O:20][C:21]4[CH:30]=[CH:29][CH:28]=[C:27]5[C:22]=4[CH2:23][CH2:24][CH2:25][C:26]5=[O:31])=[CH:18][CH:17]=3)=[C:14]3[C:9]([C:10]([C:34]([F:37])([F:36])[F:35])=[CH:11][CH:12]=[CH:13]3)=[N:8]2)=[C:4]([F:40])[CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:39]=[CH:38][C:5]([CH2:6][N:7]2[C:15]([C:16]3[CH:33]=[CH:32][C:19]([O:20][C:21]4[CH:30]=[CH:29][CH:28]=[C:27]5[C:22]=4[CH2:23][CH2:24][CH2:25][CH:26]5[OH:31])=[CH:18][CH:17]=3)=[C:14]3[C:9]([C:10]([C:34]([F:36])([F:37])[F:35])=[CH:11][CH:12]=[CH:13]3)=[N:8]2)=[C:4]([F:40])[CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67021459HCID 67021459, compound

Product 1

HCID 67021154HCID 67021154, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-{4-[2-(4-chloro-2-fluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-yl]phenoxy}-3,4-dihydronaphthalen-1(2H)-one (14 mg, 0.025 mmol) dissolved in 1.5 mL THF was added to a slurry of LiAlH4 in THF and stirred at room temperature for 2 hours. The reaction mixture was quenched with H2O and stirred for 15 min. Filtration of the mixture was followed by extraction with CH2Cl2. The combined organic phases were dried, evaporated and the crude material was purified by HPLC using a gradient with an acidic mobile phase on an ACE-C8 column to afford 1.2 mg analytically pure product.

Workup

  1. customThe reaction mixture was quenched with H2O
  2. stirringstirred for 15 min
  3. filtrationFiltration of the mixture
  4. extractionwas followed by extraction with CH2Cl2
  5. customThe combined organic phases were dried
  6. customevaporated
  7. customthe crude material was purified by HPLC
  8. customto afford 1.2 mg analytically pure product

Sources & evidence

ORD record
ord-1fc2954cd3734611932888ab24723f4a
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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