Cesium fluoride → HCID 68520287, compound

HRID 2246461Notes

Reaction equation

HRID 2246461 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]2[N:10]=[CH:11][N:12]([CH2:13][CH3:14])[C:4]=2[CH:3]=1.[Cl:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][C:21]=1[Cl:22].[F-].[Cs+]>COCCOC.CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:13]([N:12]1[C:4]2[CH:3]=[C:2]([C:19]3[CH:18]=[CH:17][C:16]([Cl:15])=[C:21]([Cl:22])[CH:20]=3)[N:7]=[C:6]([C:8]#[N:9])[C:5]=2[N:10]=[CH:11]1)[CH3:14]

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 27343303,4-Dichlorobenzeneboronic acidHCID 86613870HCID 86613870, compound

Product 1

HCID 68520287HCID 68520287, compoundYield 46.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

Tetrakis(triphenylphosphine)palladium (15 mg) was added under a nitrogen atmosphere to a mixture of 6-chloro-1-ethyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (42 mg), 3,4-dichloro-phenylboronic acid (152 mg) and cesium fluoride (100 mg) in DME (2mL) and methanol (1 mL). The mixture was heated at 80° C. for 24 hours then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by using preparative LC/MS (eluent: A: NH4HCO3 10 mM/B: CH3CN). to afford the title compound (30 mg) as a white solid. 1H NMR (CDCl3) δ: 8.20-8.15 (m, 2H); 7.94 (d, J=8 Hz, 1H); 7.91 (s, 1H); 7.58 (d, J=8 Hz, 1H); 4.37 (q, J=7 Hz, 2H); 1.65 (t, J=7 Hz, 3H). MS m/z: 317/ 319 (M+1).

Workup

  1. filtrationthen filtered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe residue was purified

Sources & evidence

ORD record
ord-7d054b8d28f4477692bd91d6e99882b3
Source dataset
uspto-grants-2010_03
Patent number
US07687515B2

Reaction notes

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