Tert-Butanesulfinamide → HCID 57906558, compound

HRID 420524Notes

Reaction equation

HRID 420524 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([CH:18]=O)=[CH:11][C:12]2[N:13]([CH:15]=[CH:16][N:17]=2)[CH:14]=1.[CH3:20][C:21]([S:24]([NH2:26])=[O:25])([CH3:23])[CH3:22]>C(Cl)Cl.[Ti]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10](/[CH:18]=[N:26]/[S:24]([C:21]([CH3:23])([CH3:22])[CH3:20])=[O:25])=[CH:11][C:12]2[N:13]([CH:15]=[CH:16][N:17]=2)[CH:14]=1

Participants

5

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 57906496HCID 57906496, compound

Product 1

HCID 57906558HCID 57906558, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 23963TitaniumCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carbaldehyde (104 mg, 0.36 mmol) in DCM (5 mL) were successively added 2-methyl-2-propane-sulfinamide (47.6 mg, 0.39 mmol) and titanium tetraisopropoxyde (0.21 mL, 0.72 mmol) at RT, then the mixture was heated at 45° C. and stirred for 14 h. The reaction mixture was cooled to RT, quenched by the successive addition of MeOH (2 mL) and several drops of a saturated NaHCO3 solution in water. The resulting precipitate was filtered through a Na2SO4 pad, the solid was washed with AcOEt and the filtrate was evaporated to dryness. The remaining residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→100% TBME) to yield the title compound (101 mg, 0.26 mmol, 72%). MS: 394 [M+1]+; HPLC: AtRet=1.58; TLC: RF 0.33 (hexane/DCM/TBME 1:1:6).

Workup

  1. customat RT
  2. temperatureThe reaction mixture was cooled to RT
  3. customquenched by the successive addition of MeOH (2 mL) and several drops of a saturated NaHCO3 solution in water
  4. filtrationThe resulting precipitate was filtered through a Na2SO4 pad
  5. washthe solid was washed with AcOEt
  6. customthe filtrate was evaporated to dryness
  7. customThe remaining residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, [hexane/DCM 1:1]/TBME 95:5→100% TBME)

Sources & evidence

ORD record
ord-979d79d585844857bdb2f545b608415d
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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