Potassium Carbonate → HCID 178506035, compound

HRID 1255500Notes

Reaction equation

HRID 1255500 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]3[C:10]([CH2:11][NH:12][CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[C@H:14]1[CH2:19][CH2:18][C@H:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][N:22]=2)[CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:37][CH2:38][F:39]>C(#N)C>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]3[C:10]([CH2:11][N:12]([CH2:37][CH2:38][F:39])[CH2:13][C:4]=2[CH:3]=1)=[N:9][N:8]=[C:7]3[C@H:14]1[CH2:19][CH2:18][C@H:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][N:22]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 178505898HCID 178505898, compound

Product 1

HCID 178506035HCID 178506035, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of trans-8-chloro-1-[4-(5-fluoro-pyridin-2-yloxy)-cyclohexyl]-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene (0.10 g, 0.24 mmol) and potassium carbonate (67 mg, 0.48 mmol) in acetonitrile (1.2 ml) was treated with 1-bromo-2-fluoroethane (37 mg, 0.29 mmol) at 0° C. The cooling bath was removed and the reaction mixture was heated at 70° C. over night. The mixture was filtered and concentrated in vacuo. Purification by flash column chromatography gave the title compound (17 mg, 15%) as white solid. MS m/e: 460 (M+H+)

Workup

  1. customThe cooling bath was removed
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-f7525db5c67444668a253805c34da0f0
Source dataset
uspto-grants-2013_06
Patent number
US08461152B2

Reaction notes

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