Sodium Carbonate → HCID 10021860, compound

HRID 891845Notes

Reaction equation

HRID 891845 reaction equation
Br[C:2]1[N:6]2[N:7]=[CH:8][C:9]([C:11]([OH:14])([CH3:13])[CH3:12])=[N:10][C:5]2=[N:4][CH:3]=1.[F:15][C:16]1[C:21]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[C:20]([F:28])[CH:19]=[CH:18][C:17]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[F:28][C:20]1[C:21]([C:22]2[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=2)=[C:16]([F:15])[CH:17]=[CH:18][C:19]=1[C:2]1[N:6]2[N:7]=[CH:8][C:9]([C:11]([OH:14])([CH3:13])[CH3:12])=[N:10][C:5]2=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 112076032-(7-Bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-olHCID 22240089HCID 22240089, compound

Product 1

HCID 10021860HCID 10021860, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(7-bromoimidazo[1,2-b][1,2,4]triazin-3-yl)propan-2-ol (0.10 g, 0.38 mmol), 2,4-difluoro-3-(pyridin-4-yl)benzeneboronic acid (0.14 g, 0.58 mmol) and sodium carbonate (950 μL of a 2 M solution) in ethylene glycol dimethyl ether (2 ml) was degassed by bubbling nitrogen through for 20 min. Tetrakis(triphenylphosphine)palladium(0) (0.02 g, 0.02 mmol) was added and the mixture was degassed for a further 20 min before heating at 80° C. for 18 h. The mixture was filtered through glass fibre paper, and partitioned between ethyl acetate (30 ml) and water (30 ml). The organic layer was dried (Na2SO4), filtered and evaporated in vacuo. Purification by chromatography (silica gel, 5% MeOH/CH2C12), then recrystallisation from EtOAc/CH2C1 2, gave 7.0 mg (5%) of the title compound: 1H NMR (360 MHz, CDCl3) δ 7.19–7.24 (1H, s), 7.47 (2H, d, J 4.6), 8.14–8.21 (1H, m), 8.28 (1H, d, J 2.5), 8.77 (3H, dd, J 4.6, 6.0).

Workup

  1. customwas degassed
  2. customby bubbling nitrogen through for 20 min
  3. customthe mixture was degassed for a further 20 min
  4. filtrationThe mixture was filtered through glass fibre paper
  5. custompartitioned between ethyl acetate (30 ml) and water (30 ml)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customPurification by chromatography (silica gel, 5% MeOH/CH2C12)
  10. customrecrystallisation from EtOAc/CH2C1 2

Sources & evidence

ORD record
ord-4e8621cd6934480cae87c73fd1a79533
Source dataset
uspto-grants-2006_02
Patent number
US07005431B2

Reaction notes

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