Sodium borohydride → 2-(4-(6-(4-(6-fluoroindolin-1-yl)piperidin-1-yl)pyridazin-3-yl)-1H-pyrazol-1-yl)ethanol

HRID 512846Notes

Reaction equation

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

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of ethyl 2-(4-(6-(4-(6-fluoroindolin-1-yl)piperidin-1-yl)pyridazin-3-yl)-1H-pyrazol-1-yl)acetate (90 mg, 0.2 mmol) in EtOH (3 mL) was added NaBH4 (76 mg, 2 mmol). The resulting mixture was heated at 65° C. for 2 h and then poured into CH2Cl2/H2O (50 mL/50 mL). The aqueous layer was extracted with CH2Cl2 (50 ml). The combined organic layer was dried (Na2SO4) and filtered. The solvent was removed and the resulting residue was purified by silica gel column using EtOAc to 2% MeOH/EtOAc as the eluent to yield 2-(4-(6-(4-(6-fluoroindolin-1-yl)piperidin-1-yl)pyridazin-3-yl)-1H-pyrazol-1-yl)ethanol.

Workup

extractionThe aqueous layer was extracted with CH2Cl2 (50 ml)
dry with materialThe combined organic layer was dried (Na2SO4)
filtrationfiltered
customThe solvent was removed
customthe resulting residue was purified by silica gel column

Sources & evidence

ORD record: ord-aff51d00d59d46e0a954fbddd272ea66
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102669B2

Reaction notes

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