Tetrabutylammonium Fluoride → HCID 57637341, compound

HRID 2078744Notes

Reaction equation

HRID 2078744 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17](C)(C)[O:18][SiH2]C(C)(C)C)=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:26]1[C:27]2[S:40][C:39]([CH2:41][N:42]3[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]3)=[CH:38][C:28]=2[N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[N:30]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][OH:18])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:26]1[C:27]2[S:40][C:39]([CH2:41][N:42]3[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]3)=[CH:38][C:28]=2[N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[N:30]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131727417HCID 131727417, compound2×

Product 1

HCID 57637341HCID 57637341, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To 2-(1-tert-butoxycarbonyl-5-piperidin-1-ylmethyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-indole-1-carboxylic acid tert-butyl ester [530 mg, 0.78 mmol, Intermediate (83)] in tetrahydrofuran (10 mL) at 0° C. was added a 1M solution of TBAF in tetrahydrofuran (0.86, 0.86 mmol). The mixture was stirred at 0° C. for 2 hours. It was diluted with ethyl acetate and washed with saturated aqueous ammonium chloride. The organic layer was dried over magnesium sulfate and concentrated. The residue was chromatographed through silica gel (n-heptane/ethyl acetate, 80/20 as eluant) to afford 2-(1-tert-butoxycarbonyl-5-piperidin-1-ylmethyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-hydroxymethyl-indole-1-carboxylic acid tert-butyl ester [305 mg, 70%, Intermediate (84)] as a white foam. LC/MS: 567.3 (M+H), RT=2.89 minutes.

Workup

  1. washwashed with saturated aqueous ammonium chloride
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was chromatographed through silica gel (n-heptane/ethyl acetate, 80/20 as eluant)

Sources & evidence

ORD record
ord-b931026f1f6c46bdb6f098c5fed6f453
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

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