Tetrahydrofuran → {5-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-[1,2,4]oxadiazol-3-yl}-methanol

HRID 658379Notes

Reaction equation

HRID 658379 reaction equation
C([O:3][C:4]([C:6]1[N: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])[O:8][N:7]=1)=O)C.C1COCC1>C(Cl)Cl.CO>[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[O:8][N:7]=[C:6]([CH2:4][OH:3])[N:10]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 590267925-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-[1,2,4]oxadiazole-3-carboxylic acid ethyl ester

Product 1

HCID 59026783{5-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-[1,2,4]oxadiazol-3-yl}-methanolYield 71.3%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 5-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-[1,2,4]oxadiazole-3-carboxylic acid ethyl ester (768 mg, 1.69 mmL, 1 eq) in THF (6 mL) LiBH4 (55 mg, 2.54 mmol, 1.5 eq) was added. The reaction mixture was stirred overnight and the solvent was evaporated. The residue was dissolved in EtOAc, washed with brine, and dried with anhydrous MgSO4. Filtration and removal of the solvent afforded the crude product which was subjected to silica gel column chromatography (eluent:CH2Cl2:MeOH 70:1) to give rise to pure product (497 mg). [5.01 min; 413 (M+1)]

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with brine
  4. dry with materialdried with anhydrous MgSO4
  5. filtrationFiltration and removal of the solvent
  6. customafforded the crude product which

Sources & evidence

ORD record
ord-fc7540c25d024c20ae873f2ffb51c5b3
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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