Methyl iodide → HCID 87870157, compound

HRID 1358047Notes

Reaction equation

HRID 1358047 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1/[CH:6]=[CH:7]/[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]2[C:24]3[C:19](=[CH:20][C:21]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:22][CH:23]=3)[CH2:18][CH2:17][N:16]2[C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)=[CH:10][CH:9]=1.[C:40](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C)C=O>[CH3:40][N:3]1[N:2]=[N:1][C:5](/[CH:6]=[CH:7]/[C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH:15]3[C:24]4[C:19](=[CH:20][C:21]([O:25][CH2:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[CH:22][CH:23]=4)[CH2:18][CH2:17][N:16]3[C:33]3[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=3)=[CH:10][CH:9]=2)=[N:4]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 18186395HCID 18186395, compound

Product 1

HCID 87870157HCID 87870157, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution containing 1-{[4-((1E)-2-(2H-1,2,3,4,-tetrazol-5-yl)vinyl)phenyl]methyl}-2-(4-fluorophenyl)-6-(phenylmethoxy)-1,2,3,4,-tetrahydroisoquinoline (430 mg, 0.831 mmol) in dimethyl formamide (12 mL) was added cesium carbonate (812 mg, 2.493 mmol) and methyl iodide (0.06 mL, 1.0 mmol). The mixture was allowed to stir at ambient temperature for 18 hours. The solvent was removed and the resulting oil was extracted with ethyl acetate and distilled water. The organic layer was dried over sodium sulfate, filtered and concentrated to afford a brown oil. The brown oil was purified by column chromatography (SiO2, 30% ethyl acetate/hexanes), to afford the title compound (100 mg, 23% yield): ES-MS (m/z) 532 [M+H]+.

Workup

  1. customThe solvent was removed
  2. extractionthe resulting oil was extracted with ethyl acetate
  3. distillationdistilled water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a brown oil
  8. customThe brown oil was purified by column chromatography (SiO2, 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9cf092d071ef403c80bff15434239a98
Source dataset
uspto-grants-2003_07
Patent number
US06593322B1

Reaction notes

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