Sodium borohydride → HCID 67021154, compound

HRID 735489Notes

Reaction equation

HRID 735489 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.[BH4-].[Na+]>CCO>[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 4311764Sodium borohydrideHCID 67021459HCID 67021459, compound

Product 1

HCID 67021154HCID 67021154, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

5-{4-[2-(4-chloro-2-fluorobenzyl)-7-(trifluoromethyl)-2H-indazol-3-yl]phenoxy}-3,4-dihydronaphthalen-1(2H)-one (330 mg, 0.58 mmol) dissolved in 10 mL of EtOH was added to a slurry of NaBH4 in EtOH and stirred at room temperature overnight. 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 a racemic mixture. Separation of the two enatiomers afforded the analytically pure products of this Example 903 and Example 936.

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 a racemic mixture
  9. customSeparation of the two enatiomers
  10. customafforded the analytically pure products of this Example 903 and Example 936

Sources & evidence

ORD record
ord-24fd118151b34d38b39b085b93f700d6
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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