Diisopropylamine → HCID 59404970, compound

HRID 1803057Notes

Reaction equation

HRID 1803057 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[Br:13][C:14]1[C:22]2[C:17](=[N:18][CH:19]=[CH:20][CH:21]=2)[S:16][CH:15]=1.[CH3:23][S:24]SC>C1COCC1>[Br:13][C:14]1[C:22]2[C:17](=[N:18][CH:19]=[CH:20][CH:21]=2)[S:16][C:15]=1[S:24][CH3:23]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 12232Dimethyl DisulfideHCID 2899263-Bromothieno[2,3-b]pyridineHCID 178418339Butyllithium

Product 1

HCID 59404970HCID 59404970, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (3.25 mL, 1.7M in hexanes, 5.2 mmol) was added to a cooled solution of diisopropylamine (0.74 mL, 5.2 mmol) in THF (15 mL) at −78° C. The reaction mixture was allowed to warm to room temperature and stirred for 30 minutes. The reaction was cooled to 0° C. and 3-bromothieno[2,3-b]pyridine (prepared by the method of Klemm L. H. et al., Journal of Heterocyclic Chemistry, 1974, 11(2), 205-209) (1 g, 4.7 mmol) added. After stirring for a further 20 minutes dimethyl disulphide (443 mg, 0.42 mL, 4.7 mmol) was added, and the reaction mixture was allowed to warm to room temperature and stirred for 1 h. The reaction was quenched with water, extracted into DCM, dried (sodium sulphate), filtered and concentrated in vacuo. Chromatography (silica; DCM) yielded the title compound as a pale yellow solid (850 mg). δH (DMSO-d6) 8.57 (1H, dd, J 4.7, 1.5 Hz), 8.00 (1H, m), 7.54 (1H, dd, J 8.1, 4.5 Hz), 2.70 (3H, m). LCMS (pH 3) RT 2.64 minutes, (ES+) 259/261 (M+H)+.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. additionwas added
  3. temperatureto warm to room temperature
  4. stirringstirred for 1 h
  5. customThe reaction was quenched with water
  6. extractionextracted into DCM
  7. dry with materialdried (sodium sulphate)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ffebe62b01a64aa5a07ca0550424cd94
Source dataset
uspto-grants-2013_01
Patent number
US08350037B2

Reaction notes

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