Acetonitrile → HCID 86695520, compound

HRID 525625Notes

Reaction equation

HRID 525625 reaction equation
[C:1](#[N:3])[CH3:2].C([Li])CCC.[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]=[N:17][S:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])=[N:14][CH:15]=1>O1CCCC1.[Cl-].[NH4+]>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]([NH:17][S:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])[CH2:2][C:1]#[N:3])=[N:14][CH:15]=1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 66893740HCID 66893740, compoundHCID 178418339Butyllithium

Product 1

HCID 86695520HCID 86695520, compoundYield 43.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of Acetonitrile (0.142 g, 3.472 mmol) in dry tetrahydrofuran (10 mL) is added n-butyl lithium (0.222 g, 3.472 mmol) at −78° C. and stir for 30 minutes at same temperature followed by drop wise addition of solution of 2-Methyl-propane-2-sulfinic acid 5-bromo-pyridin-2-ylmethyleneamide (0.5 g, 1.736 mmol) in dry tetrahydrofuran (10 mL) and stirred the reaction at −78° C. for 1 h. Reaction mixture is diluted with aqueous ammonium chloride solution and extracted with ethyl acetate. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo and purified by combi-flash chromatography using 80% ethyl acetate in hexane to afford the title compound (0.25 g): 1H-NMR (400 MHz, DMSO-d6) δ: 1.17 (s, 9H), 2.93-2.99 (m, 1H), 3.11-3.16 (m, 1H)-4.72-4.78 (m, 1H), 6.09 (d, J=9.24, 1H), 7.64 (d, J=8.44 Hz, 1H), 8.12-8.14 (dd, J1=2.36 Hz, J2=8.4 Hz, 1H), 8.674 (d, 2.24 Hz, 1H). LC-MS (m/z): [M+H]=330.0.

Workup

  1. stirringstirred
  2. customthe reaction at −78° C. for 1 h
  3. customReaction mixture
  4. extractionextracted with ethyl acetate
  5. dry with materialOrganic layer is dried over sodium sulphate, solvent
  6. customis evaporated in vacuo
  7. custompurified by combi-flash chromatography

Sources & evidence

ORD record
ord-4619b7d6812945c1b4876e3e10dc8993
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

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