Tetrabutylammonium Fluoride → HCID 57637312, compound

HRID 2078741Notes

Reaction equation

HRID 2078741 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[C:14]([C:16](C)(C)[O:17][SiH2]C(C)(C)C)[S:15][C:11]=2[C:10]([I:25])=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[C:14]([CH2:16][OH:17])[S:15][C:11]=2[C:10]([I:25])=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131727415HCID 131727415, compound2×

Product 1

HCID 57637312HCID 57637312, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To 5-(tert-butyl-dimethyl-silanyloxymethyl)-3-iodo-thieno[3,2-c]pyrazole-1-carboxylic acid tert-butyl ester [410 mg, 0.83 mmol, Intermediate (73)] in tetrahydrofuran (5 mL) was added a 1.0M TBAF solution in tetrahydrofuran (0.92 mL, 0.92 mmol) at 0° C. The solution was stirred at 0° C. for 1 hour. The solvent was removed and the residue was chromatographed through silica gel (dichloromethane/ethyl acetate, 90/10 as eluant) to afford 5-hydroxymethyl-3-iodo-thieno[3,2-c]pyrazole-1-carboxylic acid tert-butyl ester [230 mg, 73%, Intermediate (80)] as a white powder. LC/MS: 380.97 (M+H), RT=2.8 minutes.

Workup

  1. customThe solvent was removed
  2. customthe residue was chromatographed through silica gel (dichloromethane/ethyl acetate, 90/10 as eluant)

Sources & evidence

ORD record
ord-ef7ed4b8835549149037fa2a971eda6d
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

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