Tetrahydrofuran → HCID 10425720, compound

HRID 1376114Notes

Reaction equation

HRID 1376114 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[NH:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)=[CH:12][C:11]([F:22])=[CH:10][CH:9]=2)=[O:5])[CH3:2].[CH3:23]C(C)([O-])C.[K+].O1CCCC1.[Cl-].[NH4+]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:23])[C:8]2[C:13]([C:14]=1[NH:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)=[CH:12][C:11]([F:22])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 10424817HCID 10424817, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10425720HCID 10425720, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Stir at 0° C., a solution of 5-fluoro-3-(4-pyridinylamino)-1H-indole-2-carboxylic ethyl ester (0.195 mg, 0.65 mmol) in dimethylformamide (3.0 mL) and add a solution of 1M potassium tert-butoxide in tetrahydrofuran (0.8 mL, 0.8 mmol). Stir for 0.5 to 1 h at 0° C. and add lodomethane (0.05 mL, 0.78 mmol). After 1 h, add saturated aqueous ammonium chloride solution (5 mL) and ethyl acetate (10 mL). Separate the layers and reextract with ethyl acetate. Combine the organic layers and wash with water (3×'s), brine and dry with MgSO4. Concentrate the extract to obtain 60 mg (30%) of the title compound as a brown solid: ESI/MS 314 (M+H); HPLC: Rt=1.50 min.

Workup

  1. stirringStir for 0.5 to 1 h at 0° C.
  2. additionadd lodomethane (0.05 mL, 0.78 mmol)
  3. customSeparate the layers
  4. washwash with water (3×'s), brine
  5. dry with materialdry with MgSO4
  6. concentrationConcentrate the
  7. extractionextract

Sources & evidence

ORD record
ord-4ff43cb1fe3443f7a3087a1e9fa314a1
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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