Ethanesulfonamide → HCID 49819974, compound

HRID 2407399Notes

Reaction equation

HRID 2407399 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[C:10]([C:12]2[CH:13]=[N:14][CH:15]=[C:16]([CH:18]=O)[CH:17]=2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])[CH3:2].[CH2:20]([S:22]([NH2:25])(=[O:24])=[O:23])[CH3:21].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1(C)C=CC=CC=1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:6]([C:5]1[CH:8]=[CH:9][C:10]([C:12]2[CH:17]=[C:16]([CH2:18][NH:25][S:22]([CH2:20][CH3:21])(=[O:24])=[O:23])[CH:15]=[N:14][CH:13]=2)=[CH:11][C:4]=1[O:3][CH2:1][CH3:2])#[N:7]

Participants

6

Reactant 3

HCID 73702EthanesulfonamideHCID 5049666Sodium triacetoxyborohydrideHCID 595783942-Ethoxy-4-(5-formylpyridin-3-yl)benzonitrile

Product 1

HCID 49819974HCID 49819974, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

Titanium(IV) isopropoxide (234 μL, 0.800 mmol) was added dropwise to a mixture of 2-ethoxy-4-(5-formylpyridin-3-yl)benzonitrile (101 mg, 0.400 mmol), ethanesulfonamide (52.4 mg, 0.480 mmol) in toluene (20 mL). The resulting mixture was heated at 140° C. for 2 hr. After concentration, the residue was dissolved in CH2Cl2 (10 mL) and sodium triacetoxyborohydride (254 mg, 1.200 mmol) was added at room temperature. The resulting mixture was stirred overnight, and quenched with NaHCO3 solution. After filtration, extraction and concentration, the residue was purified by flash column (MeOH—CH2Cl2, v/v, 1%-3.5%) and yielded a colorless oil (100 mg) which turned to colorless solid after standing. ESI-MS m/z: 317.9 [M+H]+, 1H NMR (400 MHz, CDCl3): δ 1.40 (t, J=7.4 Hz, 3H), 1.53 (t, J=7 Hz, 3H), 3.08 (q, J=7.4 Hz, 2H), 4.25 (q, J=7 Hz, 2H), 4.43 (d, J=6.2 Hz, 2H), 4.59 (brs, 1H), 7.10 (d, J=1.4 Hz, 1H), 7.19 (dd, J=8, 1.6 Hz, 1H), 7.66 (d, J=8 Hz, 1H), 7.93 (s, 1H), 8.62 (s, 1H), 8.77 (s, 1H).

Workup

  1. concentrationAfter concentration
  2. dissolutionthe residue was dissolved in CH2Cl2 (10 mL)
  3. customquenched with NaHCO3 solution
  4. filtrationAfter filtration, extraction and concentration
  5. customthe residue was purified by flash column (MeOH—CH2Cl2, v/v, 1%-3.5%)

Sources & evidence

ORD record
ord-5dd41371d7c14ba6bef4c3ec51cd369f
Source dataset
uspto-grants-2014_08
Patent number
US08809545B2

Reaction notes

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