Sodium borohydride → 3-(2-(4-(Pyridin-2-ylamino)phenoxy)pyridin-3-yl)cyclopent-2-enol

HRID 473665Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:26]=[CH:25][C:11]([O:12][C:13]2[C:18]([C:19]3[CH2:23][CH2:22][C:21](=[O:24])[CH:20]=3)=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:10][CH:9]=1.[BH4-].[Na+]>O1CCCC1.CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:9]=[CH:10][C:11]([O:12][C:13]2[C:18]([C:19]3[CH2:23][CH2:22][CH:21]([OH:24])[CH:20]=3)=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 3-(2-(4-(pyridin-2-ylamino)phenoxy)pyridin-3-yl)cyclopent-2-enone (791 mg, 2.304 mmol, Example 1) in Tetrahydrofuran (150 mL) and Methanol (15.00 mL) was cooled to 0° C. under nitrogen, and was treated with sodium borohydride (349 mg, 9.21 mmol, 4.0 equiv) in 4 lots over 15 min. The reaction was warmed to 23° C. and was stirred under nitrogen. After 24 h, the reaction was quenched with saturated ammonium chloride solution (15 mL). The suspension was diluted with EtOAc (250 mL) and washed with saturated ammonium chloride solution (100 mL) and brine (100 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluant: 1-4% methanol/dichloromethane), affording 3-(2-(4-(pyridin-2-ylamino)phenoxy)pyridin-3-yl)cyclopent-2-enol.

Workup

temperatureThe reaction was warmed to 23° C.
customthe reaction was quenched with saturated ammonium chloride solution (15 mL)
additionThe suspension was diluted with EtOAc (250 mL)
washwashed with saturated ammonium chloride solution (100 mL) and brine (100 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
custompurified by silica gel chromatography (eluant: 1-4% methanol/dichloromethane)

Sources & evidence

ORD record: ord-dcd69e81dfbf4c35be008a0f8cd9dc69
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637500B2

Reaction notes

Loading…