Triethylamine → 1-[4-(7-Ethynyl-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamine

To a solution of 1-[4-(3-phenyl-7-trimethylsilanylethynyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamine (31 mg, 0.07 mmol) in THF (0.5 mL) was added a 1 M solution of tetra-n-butylammonium fluoride in THF (0.2 mL, 0.2 mmol, 3.0 equiv). The resulting solution was stirred at room temperature for 18 h, then was separated between water (15 mL) and EtOAc (15 mL). The aqueous layer was extracted with EtOAc (2×15 mL). The combined organic phases were washed with water (15 mL), dried (Na2SO4 anh) and concentrated under reduced pressure. The remaining material was treated with triethylamine (0.03 mL, 0.21 mmol, 3.0 equiv) and the resulting material was purified using MPLC (Biotage Isolera Flash NH2 Snap 10 reverse phase column; 100% CH2Cl2 for 8.5 min., gradient to 95% CH2Cl2: 5% MeOH over 7 min.; 95% CH2Cl2: 5% MeOH for 9 min.) to give 1-[4-(7-ethynyl-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamine (12 mg, 39%).

1. customwas separated between water (15 mL) and EtOAc (15 mL)
2. extractionThe aqueous layer was extracted with EtOAc (2×15 mL)
3. washThe combined organic phases were washed with water (15 mL)
4. dry with materialdried (Na2SO4 anh)
5. concentrationconcentrated under reduced pressure
6. customthe resulting material was purified
7. wait100% CH2Cl2 for 8.5 min.
8. waitgradient to 95% CH2Cl2: 5% MeOH over 7 min.

ORD record

ord-9c0647213af24c89925a1b94882446ad

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08975265B2