Trifluoroacetic acid → HCID 136341364, compound

HRID 1776811Notes

Reaction equation

HRID 1776811 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[N:16](C(OC(C)(C)C)=O)[C:15]3[C:10](=[N:11][C:12]([O:24][CH3:25])=[CH:13][CH:14]=3)[CH:9]=2)[C:5]([OH:26])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>ClCCl.O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[NH:16][C:15]3[C:10](=[N:11][C:12]([O:24][CH3:25])=[CH:13][CH:14]=3)[CH:9]=2)[C:5]([OH:26])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136341363HCID 136341363, compound

Product 1

HCID 136341364HCID 136341364, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 2-(6-chloro-3-hydroxypyridin-2-yl)-5-methoxy-1H-pyrrolo[3,2-b]pyridine-1-carboxylate (260 mg, 0.69 mmol) in dichloromethane (6.0 mL) was added TFA (118 mg, 1.04 mmol). The mixture was stirred at room temperature for 8 hours. The mixture was diluted with H2O and extract with EtOAc. The organics were washed with brine and dried over Na2SO4. After concentrated, the crude product of 6-chloro-2-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-2-yl)pyridin-3-ol (128 mg, yield: 67%). MS (M+H)+: 276/278.

Workup

  1. extractionextract with EtOAc
  2. washThe organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentrated

Sources & evidence

ORD record
ord-35a0822af6fe4f10bdc255b907c04fd7
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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