Tetrabutylammonium Fluoride → HCID 135495104, compound

HRID 2111185Notes

Reaction equation

HRID 2111185 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:12][C:11]2[C:10]([C:13]3[NH:14][C:15]4[C:20]([CH:21]=3)=[CH:19][C:18]([C:22](C)(C)[O:23][SiH2]C(C)(C)C)=[CH:17][CH:16]=4)=[N:9][NH:8][C:7]=2[CH:6]=1)=[O:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[S:12][C:11]2[C:10]([C:13]3[NH:14][C:15]4[C:20]([CH:21]=3)=[CH:19][C:18]([CH2:22][OH:23])=[CH:17][CH:16]=4)=[N:9][NH:8][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 154096419HCID 154096419, compound2×

Product 1

HCID 135495104HCID 135495104, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-[5-(tert-butyl-dimethyl-silanyloxymethyl)-1H-indol-2-yl]-1H-thieno[3,2-c]pyrazole-5-carboxylic acid methyl ester [192 mg, 0.435 mmol, Intermediate (28)] is dissolved in tetrahydrofuran (10 mL) and treated with tetrabutylammonium fluoride (1.0 M in tetrahydrofuran, 0.52 mL) and stirred overnight. The reaction mixture is diluted in ethyl acetate and washed with water, brine and dried over sodium sulfate. The residue is chromatographed on 10 g silica gel cartridge (50% ethyl acetate in heptane then ethyl acetate) to obtain solid. Recrystallization from ethyl acetate and heptane afforded 3-(5-hydroxymethyl-1H-indol-2-yl)-1H-thieno[3,2-c]pyrazole-5-carboxylic acid methyl ester [90 mg, 73%, Example 40] as beige solid; 1H NMR [(CD3)2SO)]: δ 13.66 (1H, s), 11.60 (1H, s), 7.92 (1H, s), 7.51 (1H, s), 7.38 (1H, d, J=8.2 Hz), 7.10 (1H, d, J=8.2 Hz), 6.68 (1H, s), 5.75 (1H, br s, OH), 4.54 (2H, s, —CH2OH), 3.90 (3H, s, —CO2CH3); LC/MS 328 (M++H).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulfate
  3. customThe residue is chromatographed on 10 g silica gel cartridge (50% ethyl acetate in heptane
  4. customethyl acetate) to obtain solid
  5. customRecrystallization from ethyl acetate and heptane

Sources & evidence

ORD record
ord-ba6f9624ac5d4ccd8ae6500bea41706d
Source dataset
uspto-grants-2009_04
Patent number
US07518000B2

Reaction notes

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