Water → HCID 15290091, compound

HRID 1757105Notes

Reaction equation

HRID 1757105 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[C:8]([C:10]3([C:17]([S:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)=[N:18][CH3:19])[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]3[OH:16])[CH:7]=[CH:6][C:5]=12.CC(C)([O-])C.[K+].[CH2:36](Br)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.O>O1CCCC1>[CH2:36]([O:16][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][C:10]1([C:8]1[CH:7]=[CH:6][C:5]2[N:4]([CH:3]=[CH:2][N:1]=2)[CH:9]=1)[C:17]([S:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)=[N:18][CH3:19])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 15290090HCID 15290090, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15290091HCID 15290091, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

1.04 g of 2-(imidazo[1,2-a]pyridin-6-yl)-2-((4-methoxybenzylthio)(methylimino)methyl)cyclohexanol was suspended in 25 ml of tetrahydrofuran. The obtained suspension was cooled to -60° C., followed by the addition of 300 mg of potassium t-butoxide at once. The obtained mixture was stirred at -60° C. for 2.5 hours, followed by the addition of 0.32 ml of benzyl bromide. The temperature of the obtained mixture was gradually raised to 0° C. in about one hour and the resulting mixture was stirred at 0° C. for 2 hours, followed by the addition of water. The obtained mixture was extracted with chloroform. The organic phase was dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (50:1)] to give 500 mg of (yield: 39%). the title compound as a pale-yellow oil

Workup

  1. temperatureThe temperature of the obtained mixture was gradually raised to 0° C. in about one hour
  2. stirringthe resulting mixture was stirred at 0° C. for 2 hours
  3. extractionThe obtained mixture was extracted with chloroform
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (50:1)]
  8. customto give 500 mg of (yield: 39%)

Sources & evidence

ORD record
ord-fcfd1eeaa7eb422587b64d0e48ecc211
Source dataset
uspto-grants-1995_08
Patent number
US05444066

Reaction notes

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