Potassium Carbonate → HCID 178477853, compound

HRID 1966005Notes

Reaction equation

HRID 1966005 reaction equation
Cl.[Cl:2][C:3]1[CH:28]=[CH:27][C:6]2[N:7]3[C:11]([CH2:12][NH:13][CH2:14][C:5]=2[CH:4]=1)=[N:10][N:9]=[C:8]3[C@H:15]1[CH2:20][CH2:19][C@H:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].Br.Br[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=1>C(#N)C>[Cl:2][C:3]1[CH:28]=[CH:27][C:6]2[N:7]3[C:11]([CH2:12][N:13]([CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=4)[CH2:14][C:5]=2[CH:4]=1)=[N:10][N:9]=[C:8]3[C@H:15]1[CH2:20][CH2:19][C@H:18]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 178478522HCID 178478522, compound

Product 1

HCID 178477853HCID 178477853, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of trans-8-chloro-1-(4-phenyl-cyclohexyl)-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene hydrochloride (0.065 g, 0.16 mmol) and potassium carbonate (0.073 ml, 0.53 mmol) in acetonitrile (1 ml) was added 2-(bromomethyl)pyridine hydrobromide (0.042 g, 0.16 mmol) at room temperature. Stirring for 65 h at 50° C. was followed by partitioning between 1 M aqueous sodium hydroxide solution (50 ml) and dichloromethane (50 ml). The layers were separated. The aqueous layer was extracted with one 50-ml portion of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash-chromatography with n-heptane/ethyl acetate as eluent gave the title compound (0.058 g, 79%) as white solid. MS m/e: 471 (M+H+)

Workup

  1. customby partitioning between 1 M aqueous sodium hydroxide solution (50 ml) and dichloromethane (50 ml)
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with one 50-ml portion of dichloromethane
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by flash-chromatography with n-heptane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-f6197d21067c4ca3898605483c10ef7b
Source dataset
uspto-grants-2013_04
Patent number
US08420633B2

Reaction notes

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