HCID 68312364, compound → HCID 68312752, compound

HRID 1472900Notes

Reaction equation

HRID 1472900 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]=[C:2]2[C:8]1[N:13]=[C:12]([CH2:14][NH:15][C@H:16]([CH:19]([CH3:21])[CH3:20])[CH2:17][OH:18])[C:11]([F:22])=[CH:10][CH:9]=1>[Pd]>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[C:8]1[N:13]=[C:12]([CH2:14][NH:15][C@H:16]([CH:19]([CH3:20])[CH3:21])[CH2:17][OH:18])[C:11]([F:22])=[CH:10][CH:9]=1

Participants

3

Reactant 1

HCID 68312364HCID 68312364, compound

Product 1

HCID 68312752HCID 68312752, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A microwave vial was charged with SiliaCat DPP-Pd (0.10 equivalent, 127 mg, purchased from Silicycle). A solution of Example 73A (100 mg, 0.30 mmol) in ethanol (1.0 mL) was added, followed by a solution of bicyclo[2.2.1]hept-2-en-2-ylboronic acid (41 mg, 0.30 mmol) in ethanol (1.0 mL) and 1 M aqueous Cs2CO3 (1.03 mL). The resulting mixture was heated in a microwave for 20 minutes at 120° C., filtered, and concentrated to provide (2R)-2-(((6-(bicyclo[2.2.1]hept-2-en-2-yl)-3-fluoropyridin-2-yl)methyl)amino)-3-methylbutan-1-ol. (2R)-2-(((6-(bicyclo[2.2.1]hept-2-en-2-yl)-3-fluoropyridin-2-yl)methyl)amino)-3-methylbutan-1-ol was subjected to hydrogenation (H2 atmosphere, Pd/C catalyst) then purified by reverse phase HPLC to provide the title compound. MS (ESI+) m/z 307 (M+H)+.

Workup

  1. customthen purified by reverse phase HPLC

Sources & evidence

ORD record
ord-d28ef42d68dd4bca9d53f14d35f01264
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

Loading…