Tetrabutylammonium Fluoride → (3-chloro-pyridin-4-ylmethyl)[5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-amine

HRID 1256825Notes

Reaction equation

HRID 1256825 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[C:12]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([NH:26][CH2:27][C:28]4[CH:29]=NC=[CH:32][C:33]=4[Cl:34])=[N:24][CH:25]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[F-].[CH2:36]([N+:40](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:34][C:33]1[CH:32]=[N:40][CH:36]=[CH:29][C:28]=1[CH2:27][NH:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C:12]2[C:13]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:10][CH:11]=2)=[CH:25][N:24]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69076090[5-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-(4-chloro-pyridin-3-ylmethyl)-amine

Product 1

HCID 25151532(3-chloro-pyridin-4-ylmethyl)[5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To [5-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-yl]-(4-chloro-pyridin-3-ylmethyl)-amine (602, 0.08 g, 0.16 mmol) in tetrahydrofuran (10.0 mL) was added tetrabutylammonium fluoride, trihydrate (0.240 g, 0.76 mmol). The reaction was stirred at room temperature overnight. The reaction was concentrated and purified by silica gel column chromatography eluting with 20% to 100% ethyl acetate in hexane to give a yellow solid (P-0183, 4.0 mg, 7%). MS (ESI) [M+H+]+=350.2.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by silica gel column chromatography
  3. washeluting with 20% to 100% ethyl acetate in hexane
  4. customto give a yellow solid (P-0183, 4.0 mg, 7%)

Sources & evidence

ORD record
ord-cd36f4a2db9849749fa21369bd811218
Source dataset
uspto-grants-2013_06
Patent number
US08461169B2

Reaction notes

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