Cesium carbonate → HCID 86667855, compound

HRID 539778Notes

Reaction equation

HRID 539778 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]#[C:24][Si](C)(C)C)=[C:19]([N+:29]([O-:31])=[O:30])[CH:18]=3)[N:16]=2)[N:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.O>[C:23]([C:20]1[CH:21]=[CH:22][C:17]([C:15]2[N:16]=[C:11]3[CH:10]=[CH:9][C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])=[N:13][N:12]3[CH:14]=2)=[CH:18][C:19]=1[N+:29]([O-:31])=[O:30])#[CH:24]

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 68089235HCID 68089235, compound

Product 1

HCID 86667855HCID 86667855, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 6-(2-fluorophenyl)-2-(3-nitro-4-((trimethylsilyl)ethynyl)phenyl)imidazo[1,2-b]pyridazine (0.250 g, 0.58 mmol) in acetonitrile (100 mL) containing catalytic cesium carbonate (0.101 mmol) in water (0.031 mL) is heated at 60° C. for 4 hours. The mixture is concentrated to dryness then purified via chromatography using CH2Cl2 to afford the title product (0.170 g, 82%) as a yellow solid: Rf 0.40 (CH2Cl2); LCMS (m/z)=359.4 [M+H]+, tR=3.02 min.

Workup

  1. concentrationThe mixture is concentrated to dryness
  2. customthen purified via chromatography

Sources & evidence

ORD record
ord-2a3c747b7fab47e2ad3e506d03919726
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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