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Sodium methanesulfinate → 10-Chloro-7-(1-ethylpropyl)-1-[3-methyl-5-(methylsulfonyl)pyridin-2-yl]-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole

HRID 1628875
Notes
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Reaction equation

HRID 1628875 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:28])[C:5]([N:8]2[C:14]3=[N:15][C:16]4[C:21]([Cl:22])=[CH:20][CH:19]=[C:18]([CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[C:17]=4[N:13]3[CH2:12][CH2:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[CH3:29][S:30]([O-:32])=[O:31].[Na+]>CN1CCCC1=O.C(OCC)(=O)C.[Cu]I>[Cl:22][C:21]1[C:16]2[N:15]=[C:14]3[N:8]([C:5]4[C:4]([CH3:28])=[CH:3][C:2]([S:30]([CH3:29])(=[O:32])=[O:31])=[CH:7][N:6]=4)[CH2:9][CH2:10][CH2:11][CH2:12][N:13]3[C:17]=2[C:18]([CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[CH:19][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 577864001-(5-bromo-3-methylpyridin-2-yl)-10-chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole

Product 1

HCID 5778610110-Chloro-7-(1-ethylpropyl)-1-[3-methyl-5-(methylsulfonyl)pyridin-2-yl]-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazoleYield 36.2%

Reagents, catalysts & solvents 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 8857Ethyl AcetateSolvent
HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 1-(5-bromo-3-methylpyridin-2-yl)-10-chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole (463 mg, 0.216 mmol), sodium methanesulfinate (66 mg, 0.648 mmol) and copper(I) iodide (123 mg, 0.648 mmol) in 1-methyl-2-pyrrolidinone (1.0 mL) was heated under microwave irradiation at 180° C. for 1 hr. After cooling, the mixture was diluted with ethyl acetate, filtered through a pad of celite, washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture followed by recrystallization from ethyl acetate/n-hexane to afford the title compound (36 mg, 36%) as a colorless solid.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered through a pad of celite
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture
  7. customfollowed by recrystallization from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-524cd8ba138a48c2a711c8605cf3a843
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08785460B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes