Tetrahydrofuran → HCID 59852884, compound

HRID 2237254Notes

Reaction equation

HRID 2237254 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[C:6]=1[C:12]#[C:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C1COCC1.[NH4+].[Cl-]>[Zn].CO>[NH2:24][C:22]1[CH:21]=[CH:20][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[C:6]=2[C:12]#[C:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[C:2]([F:1])[CH:23]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 59853062HCID 59853062, compound

Product 1

HCID 59852884HCID 59852884, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-(2-fluoro-4-nitrophenoxy)-3-(2-(pyridin-2-yl)ethynyl)pyridin-2-amine (35 mg, 0.1 mmol), THF (1.5 mL) and MeOH (1.5 ml) was treated with zinc dust (65 mg, 1.0 mmol) and NH4Cl (53 mg, 1.0 mmol) and heated at 60° C. for 45 min. The reaction mixture was cooled, filtered and concentrated under vacuum. The residue was partitioned between EtOAc and saturated aq. NaHCO3 solution. The organic phase was separated, washed with brine, dried (MgSO4) and concentrated to give the title compound (25 mg, 78%) as a brown solid. MS(ESI+): m/z 321.2 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated under vacuum
  4. customThe residue was partitioned between EtOAc and saturated aq. NaHCO3 solution
  5. customThe organic phase was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-edd895ff9acc44c1965151667068b5fb
Source dataset
uspto-grants-2010_05
Patent number
US07714138B2

Reaction notes

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