Tetrahydrofuran → HCID 178520013, compound

HRID 658375Notes

Reaction equation

HRID 658375 reaction equation
C([O:3][C:4]([C:6]1[NH:10][C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[NH:17][C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=2[F:25])=[N:8][N:7]=1)=O)C.C1COCC1>>[F:25][C:19]1[CH:20]=[C:21]([I:24])[CH:22]=[CH:23][C:18]=1[NH:17][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:11]=1[C:9]1[NH:10][C:6]([CH2:4][OH:3])=[N:7][N:8]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 178470462HCID 178470462, compound

Product 1

HCID 178520013HCID 178520013, compoundYield 30.2%

Procedure

To a solution of 5-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-4H-[1,2,4]triazole-3-carboxylic acid ethyl ester (150 mg, 0.33 mmol, 1 eq) in THF (3 mL) LiBH4 (10.8 mg, 0.5 mmol, 1.5 eq) was added. The reaction mixture was stirred overnight at RT. The solvent was evaporated and the residue was dissolved in EtOAc, washed with brine, and dried over MgSO4. After filtration and solvent removal, the crude product was purified by preparative HPLC, to afford the desired product (41 mg). [5.57 min; 454 (M+1)]

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration and solvent removal
  6. customthe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-cee85931ec514817be70cf6328420bc5
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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