Borane → HCID 69218580, compound

HRID 272719Notes

Reaction equation

HRID 272719 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][C:10]=1[I:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].B>C1COCC1>[OH:14][CH2:13][C:12]1[CH:16]=[CH:17][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[C:10]([I:18])[CH:11]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 69217291HCID 69217291, compound

Product 1

HCID 69218580HCID 69218580, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of Example 511B (363 mg, 1.0 mmol) in THF (2 mL) at 0° C. was slowly treated with a 1.0M solution of borane in THF (2.0 mL, 2.0 mmol), allowed to reach room temperature, slowly quenched with a saturated solution of ammonium chloride and extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by column chromatography on silica gel to provide 275 mg (79%) of the desired product. MS (ESI) m/e 350 (M+H)+; 1H NMR (300 MHz, DMSO-d6) 8.44 (s, 1H), 7.77 (d, J=0.7 Hz, 1H), 7.25-7.32 (m, 2H), 5.25 (t, J=5.8 Hz, 1H), 4.44 (d, J=5.4 Hz, 2H), 1.45 (s, 9H).

Workup

  1. customto reach room temperature
  2. customslowly quenched with a saturated solution of ammonium chloride
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-258cc78655624df0a8a4cabe59d19719
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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