Sodium borohydride → 1-[4-Chloro-5-(2-hydroxyethyl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol

HRID 244458Notes

Reaction equation

HRID 244458 reaction equation
[Cl:1][C:2]1[C:3]2[N:10]([CH2:11][CH:12]=[O:13])[CH:9]=[C:8]([C:14]([C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[N:25]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[N:24]=[CH:23]4)([OH:19])[C:15]([F:18])([F:17])[F:16])[C:4]=2[N:5]=[CH:6][N:7]=1.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[C:3]2[N:10]([CH2:11][CH2:12][OH:13])[CH:9]=[C:8]([C:14]([C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[N:25]([C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)[N:24]=[CH:23]4)([OH:19])[C:15]([F:18])([F:17])[F:16])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59437308(4-chloro-7-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[3,2-d]pyrimidin-5-yl)acetaldehyde

Product 1

HCID 249579921-[4-Chloro-5-(2-hydroxyethyl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanolYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of (4-chloro-7-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[3,2-d]pyrimidin-5-yl)acetaldehyde (91 mg, 0.18 mmol) in 3 mL of THF was added NaBH4 (4 mg, 0.09 mmol, 0.5 equiv.). After 2 hours, the reaction was quenched with water and extracted with EtOAc. The organics were dried, filtered, and concentrated in vacuo. The residue was purified by HPLC (5-95% CH3CN/water 0.1% TFA). The desired peaks were combined, made basic with saturated aqueous sodium bicarbonate, and concentrated to remove excess CH3CN. The resulting aqueous layer was then extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo to provide 48 mg (53%) of the title compound as a white solid. MS m/z 506.34 (MH+).

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with EtOAc
  3. customThe organics were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by HPLC (5-95% CH3CN/water 0.1% TFA)
  7. concentrationconcentrated
  8. customto remove excess CH3CN
  9. extractionThe resulting aqueous layer was then extracted with EtOAc
  10. customThe combined organic layers were dried
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-33a4cb2f2a39469a8c863b78475becb8
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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