Water → HCID 23449254, compound

HRID 989836Notes

Reaction equation

HRID 989836 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[CH2:16]([Sn:20](Cl)([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19].[F:30][C:31]1[N:32]=[CH:33][N:34]2[CH:38]=[CH:37][S:36][C:35]=12.O>C1COCC1>[F:30][C:31]1[N:32]=[CH:33][N:34]2[CH:38]=[C:37]([Sn:20]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:16][CH2:17][CH2:18][CH3:19])[S:36][C:35]=12

Participants

6

Reactant 4

HCID 962WaterHCID 15096Tributyltin ChlorideHCID 23449270HCID 23449270, compoundHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 23449254HCID 23449254, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.0 N lithiumbis(trimethylsilyl)amide/THF solution (3.2 ml) and 0.75 ml of tri-n-butylstannyl chloride were added in that order to a solution of 7-fluoroimidazo[5,1-b]thiazole in dry THF in an argon atmosphere at −78° C. The mixture was stirred at the same temperature for 10 min. Water was added thereto, followed by extraction with ethyl acetate and washing with saturated brine. The extract was dried over anhydrous magnesium sulfate and then filtered. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=7:1) to give 820 mg of the title compound.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washwashing with saturated brine
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=7:1)

Sources & evidence

ORD record
ord-3ae4c8fbb31e4e62bd86da90d26d62ee
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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