Ammonium Chloride → HCID 22504383, compound

HRID 1814129Notes

Reaction equation

HRID 1814129 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([S:19][CH3:20])[CH:18]=[C:13]3[CH:12]=[C:11]2[Si](C)(C)C)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[Cl-].[NH4+]>O1CCCC1>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([S:19][CH3:20])[CH:18]=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 11078149TBAF tetrahydrofuranHCID 22504425HCID 22504425, compound

Product 1

HCID 22504383HCID 22504383, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-25 °C

Procedure

A mixture of 1-benzenesulfonyl-2-trimethylsilyl-5-methylthio-1H-pyrrolo[2,3-b]pyridine obtained in Example 33 (1) (0.60 g), tetrabutylammonium fluoride/tetrahydrofuran solution (1.0 M, 0.8 ml) and tetrahydrofuran (100 ml) was stirred under nitrogen atmosphere at −25° C. for 30 minutes. To the reaction solution was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain 0.40 g of the desired product.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f2c092d8756c4cb2800217118b752235
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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