Tetrahydrofuran → HCID 15982219, compound

HRID 1367283Notes

Reaction equation

HRID 1367283 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]=1[CH2:21][C:22]1[C:30]2[C:25](=[N:26][CH:27]=[CH:28][CH:29]=2)[N:24]([Si](C(C)C)(C(C)C)C(C)C)[CH:23]=1.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:20])[F:18])=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]=1[CH2:21][C:22]1[C:30]2[C:25](=[N:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 59593309HCID 59593309, compound

Product 1

HCID 15982219HCID 15982219, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To [6-Methoxy-5-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-(4-trifluoromethyl-benzyl)-amine (31, 0.0340 g, 0.0598 mmol) was added tetrahydrofuran (5 mL) followed by tetra-n-butylammonium fluoride (1M solution in tetrahydrofuran, 66 μL, 0.0658 mmol). The reaction was allowed to stir at room temperature for 2 hours, then poured into 1:1 water:saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was separated, dried over magnesium sulfate, filtered and the volatiles were removed by rotary evaporation. The resulting residue was purified by silica gel column chromatography, eluting with dichloromethane followed by 1% methanol in dichloromethane and finally 3% methanol in dichloromethane. This provided 20 mg of the desired compound as a white solid (P-0012, 0.048 mmol, 81%). MS(ESI) [M+H+]+=413.2.

Workup

  1. extractionsaturated sodium bicarbonate and extracted with ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe volatiles were removed by rotary evaporation
  6. customThe resulting residue was purified by silica gel column chromatography
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-9905eba60a884c6986d3ee1f62d37a5e
Source dataset
uspto-grants-2011_02
Patent number
US07893075B2

Reaction notes

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