Potassium Carbonate → 2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)-5-(prop-1-en-2-yl)furo[2,3-b]pyridine-3-carboxamide

HRID 2190176Notes

Reaction equation

HRID 2190176 reaction equation
[CH2:1]=[C:2]([Mg]Br)[CH3:3].B(OC(C)C)(OC(C)C)OC(C)C.C([O-])([O-])=O.[K+].[K+].[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[O:46][C:35]3=[N:36][C:37]([NH:41][S:42]([CH3:45])(=[O:44])=[O:43])=[C:38](I)[CH:39]=[C:34]3[C:33]=2[C:47]([NH:49][CH3:50])=[O:48])=[CH:28][CH:27]=1>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:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[O:46][C:35]3=[N:36][C:37]([NH:41][S:42]([CH3:45])(=[O:44])=[O:43])=[C:38]([C:2]([CH3:3])=[CH2:1])[CH:39]=[C:34]3[C:33]=2[C:47]([NH:49][CH3:50])=[O:48])=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 21531Triisopropyl borateHCID 580523242-(4-fluorophenyl)-5-iodo-N-methyl-6-(methylsulfonamido)furo[2,3-b]pyridine-3-carboxamideHCID 178456138HCID 178456138, compound

Product 1

HCID 580523332-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)-5-(prop-1-en-2-yl)furo[2,3-b]pyridine-3-carboxamideYield 73%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
0 °C

Procedure

To prop-1-en-2-ylmagnesium bromide (0.5 M THF solution, 6.1 ml, 5 eq.) in a heatgun-dried microwave tube at 0° C. was added triisopropyl borate (0.71 ml, 5 eq.). The mixture was stirred at 0° C. for 15 min and warmed to rt. K2CO3 (2 M aq. solution, 1.5 ml, 5 eq.) was added. The mixture was stirred at rt for 15 min. 2-(4-Fluorophenyl)-5-iodo-N-methyl-6-(methylsulfonamido)furo[2,3-b]pyridine-3-carboxamide (300 mg, 1 eq.) and Pd(PPh3)4 (106 mg, 0.15 eq.) were added. The mixture was degassed, stirred in a microwave reactor at 120° C. for 20 min and cooled. Water was added followed by LiOH (1 M aq. solution, 1.8 ml). The mixture was washed with ether. (It took a long time for layers to settle. There may be a solid meta-phase which can be filtered out as pure product.) Aq. layer was acidified to pH 3.5 using saturated citric acid. Precipitate was filtered, washed with water and lyophilized to give the title compound as an off-white solid (180 mg, 73%). MS (ESI) m/z 404.2 (M+1). Retention time=1.23 min (Method A).

Workup

  1. temperaturewarmed to rt
  2. stirringThe mixture was stirred at rt for 15 min
  3. customThe mixture was degassed
  4. stirringstirred in a microwave reactor at 120° C. for 20 min
  5. temperaturecooled
  6. additionWater was added
  7. washThe mixture was washed with ether
  8. filtrationcan be filtered out as pure product
  9. filtrationPrecipitate was filtered
  10. washwashed with water

Sources & evidence

ORD record
ord-7d1c40db8f27497eb80369e553ca1814
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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