Iodoethane → HCID 89614446, compound

HRID 512842Notes

Reaction equation

HRID 512842 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:22]=[N:21][C:20]([N:23]4[CH:27]=[C:26]([CH2:28][OH:29])[CH:25]=[N:24]4)=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[CH2:30](I)[CH3:31].C1COCC1.[H-].[Na+]>CCOCC.O.CN(C=O)C>[CH2:30]([O:29][CH2:28][C:26]1[CH:25]=[N:24][N:23]([C:20]2[N:21]=[N:22][C:17]([N:14]3[CH2:15][CH2:16][CH:11]([N:8]4[C:9]5[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:10]=5)[CH2:6][CH2:7]4)[CH2:12][CH2:13]3)=[CH:18][CH:19]=2)[CH:27]=1)[CH3:31]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 76314719HCID 76314719, compound

Product 1

HCID 89614446HCID 89614446, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584184Diethylether waterSolvent

Procedure

To a mixture of (1-(6-(4-(6-fluoroindolin-1-yl)piperidin-1-yl)pyridazin-3-yl)-1H-pyrazol-4-yl)methanol (59 mg, 0.15 mmol, 1 equiv) and ethyl iodide (93 mg, 0.6 mmol, 4 equiv) was added solvent THF (5 mL) and DMF (1 mL). NaH (36 mg, 60% in mineral oil, 0.9 mmol, 6 equiv) was then added. The resulting mixture was stirred at room temperature for 1.5 h and then poured into Et2O/H2O (20 mL/20 mL). The organic layer was washed with brine (20 mL), dried (Na2SO4), and filtered. The solvent was removed and the resulting residue was purified by column using 40-60% EtOAc/hexane as the eluent to yield 1-(1-(6-(4-(ethoxymethyl)-1H-pyrazol-1-yl)pyridazin-3-yl)piperidin-4-yl)-6-fluoroindoline, which was then re-crystallized from CH2Cl2/hexane upon slow evaporation.

Workup

  1. washThe organic layer was washed with brine (20 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe solvent was removed
  5. customthe resulting residue was purified by column

Sources & evidence

ORD record
ord-d9c59381dff042d18aa91ccec5287ddc
Source dataset
uspto-grants-2015_08
Patent number
US09102669B2

Reaction notes

Loading…