Tetrabutylammonium Fluoride → 3-(5-hydroxymethyl-2-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4-(7-methyl-1H-indol-3-yl)-pyrrole-2,5-dione

HRID 216653Notes

Reaction equation

HRID 216653 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([SiH2][O:24][C:25](C1C=CC=CC=1)(C1C=CC=CC=1)[C:26]1[CH:31]=[CH:30][N:29]2[N:32]=[C:33]([CH3:52])[C:34]([C:35]3[C:36](=[O:51])[NH:37][C:38](=[O:50])[C:39]=3[C:40]3[C:48]4[C:43](=[C:44]([CH3:49])[CH:45]=[CH:46][CH:47]=4)[NH:42][CH:41]=3)=[C:28]2[CH:27]=1)(C)(C)C>C1COCC1>[OH:24][CH2:25][C:26]1[CH:31]=[CH:30][N:29]2[N:32]=[C:33]([CH3:52])[C:34]([C:35]3[C:36](=[O:51])[NH:37][C:38](=[O:50])[C:39]=3[C:40]3[C:48]4[C:43](=[C:44]([CH3:49])[CH:45]=[CH:46][CH:47]=4)[NH:42][CH:41]=3)=[C:28]2[CH:27]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 1317297473-[5-[tert-butylsilyloxy(diphenyl)methyl]-2-methylpyrazolo[1,5-a]pyridin-3-yl]-4-(7-methyl-1H-indol-3-yl)pyrrole-2,5-dione

Product 1

HCID 591920083-(5-hydroxymethyl-2-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4-(7-methyl-1H-indol-3-yl)-pyrrole-2,5-dioneYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1.0 M in THF, 1.4 ml, 1.4 mmol, 1.1 equiv) is added to a solution of 3-[5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-pyrazolo[1,5-a]pyridin-3-yl]-4-(7-methyl-1H-indol-3-yl)-pyrrole-2,5-dione in THF (10 ml). The reaction mixture is stirred for 1 hour at room temperature. The solvent is removed in vacuo, and the residue is purified by flash chromatography (gradient of hexane/EtOAc 100:0 to 20:80) to afford the title compound (400 mg, 84%). 1H NMR (400 MHz, d6-DMSO): δ=11.85 (br s, 1H), 10.99 (br s, 1H), 8.53 (d, J=7.8 Hz, 1H), 7.94 (d, J=2.7 Hz, 1H), 7.35-7.34 (m, 1H), 6.82-6.79 (m, 2 H), 6.51 (t, J=8.1 Hz, 1H), 6.22 (d, J=8.1 Hz, 1H), 5.38 (t, J=5.7 Hz, 1H), 4.45 (d, J=4.9 Hz, 1H), 2.45 (s, 3H), 1.79 (s, 3H). MS (ES+): 387 (M+H)+.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by flash chromatography (gradient of hexane/EtOAc 100:0 to 20:80)

Sources & evidence

ORD record
ord-b92e0742c93d4058a41458ff3703f107
Source dataset
uspto-grants-2012_06
Patent number
US08193236B2

Reaction notes

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