Iodoethane → HCID 24825701, compound

HRID 2089513Notes

Reaction equation

HRID 2089513 reaction equation
[F:1][C:2]1([F:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([N:11]2[C:15]([CH2:16][OH:17])=[CH:14][N:13]=[CH:12]2)[C:3]1([CH3:19])[CH3:18].[H-].[Na+].I[CH2:24][CH3:25]>CN(C=O)C.C([O-])(O)=O.[Na+].C(OCC)(=O)C>[F:20][C:2]1([F:1])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([N:11]2[C:15]([CH2:16][O:17][CH2:24][CH3:25])=[CH:14][N:13]=[CH:12]2)[C:3]1([CH3:18])[CH3:19]

Participants

7

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 59199368HCID 59199368, compound

Product 1

HCID 24825701HCID 24825701, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of [3-(3,3-difluoro-2,2-dimethyl-indan-1-yl)-3H-imidazol-4-yl]-methanol, (160 mg, 0.575 mmol) in DMF (5 mL) is added a 60% dispersion of NaH in oil (46 mg, 1.15 mmol). The reaction is permitted to stir for 30 minutes at room temperature, at which time iodoethane (0.05 mL, 0.63 mmol) is added. The reaction is permitted to stir for 2 hours at which time it is diluted with saturated aqueous NaHCO3 and ethyl acetate. The layers are separated and the organic layer is dried with Na2SO4, filtered and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 0:1 to 1:6) to furnish 1-(3,3-difluoro-2,2-dimethyl-indan-1-yl)-5-ethoxymethyl-1H-imidazole; HRMS: (ESI) m/z 307.1634 [(M+H)+: Calcd for C17H21N2OF2: 307.1622]; 1H NMR (400 MHz, CDCl3) δ ppm 0.94 (d, J=2.5 Hz, 3 H), 1.28 (t, J=7.1 Hz, 3 H), 1.33 (d, J=3.3 Hz, 3 H), 3.51-3.68 (m, 2 H), 4.54-4.70 (m, 2 H), 5.58 (br. s., 1 H), 7.19 (s, 1 H), 7.23-7.26 (m, 1 H), 7.34 (s, 1 H), 7.55-7.63 (m, 2 H), 7.69-7.76 (m, 1 H).

Workup

  1. additionis added
  2. customThe layers are separated
  3. dry with materialthe organic layer is dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue is purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 0:1 to 1:6)

Sources & evidence

ORD record
ord-591231d873f34a97b5f439d71d380435
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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