N-(4-(3-(2,3-Dihydrofuran-2-YL)pyridin-2-yloxy)phenyl)pyridin-2-amine → N-(4-(3-(Tetrahydrofuran-2-YL)pyridin-2-yloxy)phenyl)pyridin-2-amine
Reaction equation
[O:1]1[CH:5]=[CH:4][CH2:3][CH:2]1[C:6]1[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:15][CH:14]=2)=[N:8][CH:9]=[CH:10][CH:11]=1>[Pd].C(O)C>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:15][CH:14]=2)=[N:8][CH:9]=[CH:10][CH:11]=1Participants
Procedure
To a 150 mL round bottom flask was added N-(4-(3-(2,3-dihydrofuran-2-yl)pyridin-2-yloxy)phenyl)pyridin-2-amine (660 mg, 1.992 mmol) and ethanol (7967 μL) before adding palladium, 10% wt. on activated carbon (70 mg, 0.658 mmol) portionwise. The flask was evacuated and backfilled with hydrogen under atmospheric pressure before allowing to stir at room temperature under hydrogen. The reaction was complete after 3 h. After dilution with ethyl acetate, the black suspension was filtered through a pad of Celite while rinsing with ethyl acetate (3×25 mL) before concentrating to a pale yellow residue. The residue was taken up in 5 mL DCM and applied directly to silica for purification (0 to 50% ethyl acetate/hexanes over 35 minutes). The target compound was isolated as a white solid. MS (ESI, pos. ion) m/z: 334.2 (M+1). IC50 (uM) 0.225.
Workup
- customThe flask was evacuated
- filtrationAfter dilution with ethyl acetate, the black suspension was filtered through a pad of Celite
- washwhile rinsing with ethyl acetate (3×25 mL)
- concentrationbefore concentrating to a pale yellow residue
- customapplied directly to silica for purification (0 to 50% ethyl acetate/hexanes over 35 minutes)
- customThe target compound was isolated as a white solid
Sources & evidence
- ORD record
- ord-e4d0120a7f3940919a6f00aaa8c9b35c
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637500B2
Reaction notes
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