Sodium Bicarbonate → HCID 178464547, compound

HRID 585902Notes

Reaction equation

HRID 585902 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH:19]=1)=[CH:8][CH:9]=[C:10]1[C:14]=2[N:13]([CH2:15][CH:16]([NH2:18])[CH3:17])[N:12]=[CH:11]1.[B-](Br)(Br)(Br)[S+](C)C.C([O-])(O)=O.[Na+]>ClCCCl>[NH2:18][CH:16]([CH3:17])[CH2:15][N:13]1[C:14]2[C:10](=[CH:9][CH:8]=[C:7]3[CH:19]=[C:3]([OH:2])[CH:4]=[CH:5][C:6]3=2)[CH:11]=[N:12]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4181510Tribromoborane-methyl sulfideHCID 22338310HCID 22338310, compound

Product 1

HCID 178464547HCID 178464547, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of the product from Step D (26 mg, 0.1 mmol) in 1,2-dichloroethane (16 mL) was added boron tribromide-methylsulfide complex (1.0 M, 1.0 mL, 1.0 mmol) and the solution stirred at reflux for 72 h. The solution was poured into aqueous NaHCO3, and extracted with ethyl acetate (2×20 mL). The combined extracts were dried (MgSO4) concentrated to a residue, which was purified by chromatography (silica, gradient, 10 to 25% methanol in dichloromethane) to furnish a solid (8 mg, 32%): 1H NMR (CDCl3) δ 8.30 (d, J=9.0 Hz, 1H), 7.99 (s, 1H), 7.60 (d, J=8.4 Hz, 1H), 7.35 (d, J=9.0 Hz, 1H), 7.29 (d, J=2.4 Hz, 1H), 7.21 (dd, J=9.0, 2.4 Hz, 1H), 3.6 (m, 1H), 3.3 (m, 2H), 1.25 (d, J=6.6 Hz, 3H); MS m/z 242 [M+H]+.

Workup

  1. temperatureat reflux for 72 h
  2. extractionextracted with ethyl acetate (2×20 mL)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated to a residue, which
  5. customwas purified by chromatography (silica, gradient, 10 to 25% methanol in dichloromethane)

Sources & evidence

ORD record
ord-07a713290fb14d44899adb5ad82388f4
Source dataset
uspto-grants-2005_08
Patent number
US06933392B2

Reaction notes

Loading…