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

HRID 872351Notes

Reaction equation

HRID 872351 reaction equation
[C:1]1([C:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:16]#[C:17][Si](C)(C)C)=[CH:15][C:10]3=[N:9][C:8]=2[C:22]2[CH:27]=[CH:26][C:25]([C:28]3([NH2:32])[CH2:31][CH2:30][CH2:29]3)=[CH:24][CH:23]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(N(CC)CC)C>C1COCC1>[C:16]([C:14]1[CH:13]=[CH:12][N:11]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:8]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4([NH2:32])[CH2:29][CH2:30][CH2:31]4)=[CH:24][CH:23]=3)[N:9]=[C:10]2[CH:15]=1)#[CH:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 666650621-[4-(3-Phenyl-7-trimethylsilanylethynyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamine

Product 1

HCID 866910431-[4-(7-Ethynyl-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamineYield 47.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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%).

Workup

  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.

Sources & evidence

ORD record
ord-9c0647213af24c89925a1b94882446ad
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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