Tetrabutylammonium Fluoride → 3-[6-(4-Trifluoromethyl-benzylamino)-pyridin-3-ylmethyl]-1H-pyrrolo[2,3-b]pyridin-5-ol

HRID 1024208Notes

Reaction equation

HRID 1024208 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:37]=[CH:36][C:6]([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]3[C:24]4[C:19](=[N:20][CH:21]=[C:22]([O:25][Si](C(C)C)(C(C)C)C(C)C)[CH:23]=4)[NH:18][CH:17]=3)=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:39][C:2]([F:1])([F:38])[C:3]1[CH:37]=[CH:36][C:6]([CH2:7][NH:8][C:9]2[N:10]=[CH:11][C:12]([CH2:15][C:16]3[C:24]4[C:19](=[N:20][CH:21]=[C:22]([OH:25])[CH:23]=4)[NH:18][CH:17]=3)=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59593366(4-Trifluoromethyl-benzyl)-[5-(5-triisopropylsilanyloxy-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-amine

Product 1

HCID 595933253-[6-(4-Trifluoromethyl-benzylamino)-pyridin-3-ylmethyl]-1H-pyrrolo[2,3-b]pyridin-5-olYield 67.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (4-Trifluoromethyl-benzyl)-[5-(5-triisopropylsilanyloxy-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-amine (85, 0.13 g, 0.23 mmol) in tetrahydrofuran (10 mL) was added tetrabutylammonium fluoride (3 mL, 1.0M in tetrahydrofuran, 3 mmol). The reaction mixture was stirred at room temperature overnight, and then was stirred at 65° C. for 48 hours. The reaction mixture was concentrated and purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as a viscous liquid (P-0061, 0.062 g, 66%). MS (ESI) [M+H+]+=399.19.

Workup

  1. stirringwas stirred at 65° C. for 48 hours
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by silica gel column chromatography
  4. washeluting with ethyl acetate in hexane

Sources & evidence

ORD record
ord-7bb5d0cf2ac640a19835afadf30dd2ab
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

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