Tetrahydrofuran → HCID 24764557, compound

HRID 1255158Notes

Reaction equation

HRID 1255158 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[C:10]([CH3:12])[N:11]=1)=O.C1COCC1>>[F:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:2]([F:1])[C:3]=1[CH2:4][NH:6][C:7]1[S:8][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:21])([F:22])[F:20])[CH:14]=2)=[C:10]([CH3:12])[N:11]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 16664613HCID 16664613, compound

Product 1

HCID 24764557HCID 24764557, compoundYield 34.2%

Conditions

Temperature
60 °C

Procedure

Into solution of Compound 9 (75.0 mg, 0.19 mmol) at room temperature was added a solution of 1.0M borane-dimethylsulfide complex in THF (1.0 mL, 1.0 mmol). The mixture was heated to 60° C. overnight, cooled to room temperature, quenched by addition of water, extracted with CH2Cl2. The extracts were dried (Na2SO4), filtered and concentrated. The residue was purified on silica to give Compound 115 (25.0 mg).

Workup

  1. temperaturecooled to room temperature
  2. customquenched by addition of water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica

Sources & evidence

ORD record
ord-3a8c9fabda964e32a36beaac70c780df
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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