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

HRID 1952148Notes

Reaction equation

HRID 1952148 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-94a598c034054df6ac5231edca1464db
Source dataset
uspto-grants-2013_03
Patent number
US08404700B2

Reaction notes

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