Methyl iodide → HCID 58497222, compound

HRID 1254076Notes

Reaction equation

HRID 1254076 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[NH:10][CH:11]=[C:12]([C:14]4[CH:15]=[CH:16][C:17]([C:20]([OH:23])([CH3:22])[CH3:21])=[N:18][CH:19]=4)[N:13]=3)[CH:5]=2)[CH2:3][CH2:2]1.[C:24](=O)([O-])[O-].[Cs+].[Cs+].CI>C1COCC1.CCOC(C)=O>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[N:10]([CH3:24])[CH:11]=[C:12]([C:14]4[CH:15]=[CH:16][C:17]([C:20]([OH:23])([CH3:21])[CH3:22])=[N:18][CH:19]=4)[N:13]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178458240HCID 178458240, compound

Product 1

HCID 58497222HCID 58497222, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of product from Step 4 (60 mg, 0.193 mmol) in THF (1 ml) was added cesium carbonate (126 mg, 0.387 mmol). After being stirred for 10 min, CH3I (0.013 ml, 0.213 mmol) was added and the reaction was stirred for 4 hrs. The reaction mixture was diluted with EtOAc, washed with NaHCO3 (sat), dried, concentrated, and separated by prep TLC (hex:EtOAc:CH3OH=6:5:1) to give 2-{5-[2-(5-cyclopropylisoxazol-3-yl)-1-methyl-1H-imidazol-4-yl]pyridin-2-yl}propan-2-ol (45 mg) LCMS: [M+H]+=325.3.

Workup

  1. stirringthe reaction was stirred for 4 hrs
  2. washwashed with NaHCO3 (sat)
  3. customdried
  4. concentrationconcentrated
  5. customseparated by prep TLC (hex:EtOAc:CH3OH=6:5:1)

Sources & evidence

ORD record
ord-12c7f39a478449a6b9b083861d3b8f95
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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