Tetrahydrofuran → HCID 58094746, compound

HRID 2282136Notes

Reaction equation

HRID 2282136 reaction equation
[C:1]([C:3]1[C:4]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])=[C:5]([C:15](N(OC)C)=[O:16])[S:6][C:7]=1[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([F:14])[CH:9]=1)#[N:2].O1CCCC1.[H-].C([Al+]CC(C)C)C(C)C>>[Cl:28][C:22]1[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[C:4]1[C:3]([C:1]#[N:2])=[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([F:14])[CH:9]=2)[S:6][C:5]=1[CH:15]=[O:16]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21225700DiisobutylaluminumhydrideHCID 58094879HCID 58094879, compound

Product 1

HCID 58094746HCID 58094746, compoundYield 74.3%

Conditions

Temperature
-78 °C

Procedure

To a dried flask were added 4-cyano-3-(2,4-dichlorophenyl)-5-(2-fluoropyridin-4-yl)-N-methoxy-N-methylthiophene-2-carboxamide (1.511 g, 3.463 mmol) and Tetrahydrofuran (91 mmol, 91 mmol). The mixture was cooled to −78° C. and Diisobutylaluminum hydride (17.3 mmol, 17.3 mmol) in hexanes was added. The mixture was stirred at the same temperature for 1 h and then raised to at 0° C. for 15 min. The reaction was quenched by ammonium chloride solution and the mixture was extracted with EtOAc. The organic layer was collected and dried. After evaporation, the residue was purified by column chromatography to afford the title compound (0.97 g, 67%). LC/MS (FA) ES+ 377, 379.

Workup

  1. temperatureraised to at 0° C. for 15 min
  2. customThe reaction was quenched by ammonium chloride solution
  3. extractionthe mixture was extracted with EtOAc
  4. customThe organic layer was collected
  5. customdried
  6. customAfter evaporation
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-842878d2cc3d40aba135042f5e4f48a5
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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