Potassium Carbonate → HCID 58052299, compound

HRID 2190164Notes

Reaction equation

HRID 2190164 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:28]([C:29](=[O:32])[NH:30][CH3:31])=[C:27]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)[O:26][C:5]2=[N:6][C:7]=1[N:8]([CH2:13][CH2:14][CH2:15][C:16]([CH3:25])([CH3:24])[C:17]([O:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[O:18])[S:9]([CH3:12])(=[O:11])=[O:10].[CH:40]1([B-](F)(F)F)[CH2:42][CH2:41]1.[K+].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH:40]1([C:2]2[CH:3]=[C:4]3[C:28]([C:29](=[O:32])[NH:30][CH3:31])=[C:27]([C:33]4[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][CH:38]=4)[O:26][C:5]3=[N:6][C:7]=2[N:8]([CH2:13][CH2:14][CH2:15][C:16]([CH3:24])([CH3:25])[C:17]([O:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[O:18])[S:9]([CH3:12])(=[O:11])=[O:10])[CH2:42][CH2:41]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23697338Potassium cyclopropyltrifluoroborateHCID 58052330HCID 58052330, compound

Product 1

HCID 58052299HCID 58052299, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
116 °C

Procedure

Isobutyl 5-(N-(5-iodo-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6-yl)methylsulfonamido)-2,2-dimethylpentanoate (70 mg, 0.086 mmol) is dissolved in toluene (6 mL) and a premixed solution of potassium cyclopropyltrifluoroborate (155 mg, 1.045 mmol) and potassium carbonate (2M, 0.62 mL, 1.255 mmol) is added followed by Pd(Ph3)4 (3.6 mg, 3.14 umol). The mixture is degassed for 10 min then heated at 116° C. for 20 min in the microwave. The reaction mixture is then filtered through celite and aqueous extracted with EtOAc (3×15 mL). The organic is then washed with Brine (10 mL) and dried over Na2SO4 and concentrated. HPLC purification gives 50 mg (82% yield) of isobutyl 5-(N-(5-cyclopropyl-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6-yl)methylsulfonamido)-2,2-dimethylpentanoate. MS-ES [M+H]+=584.3. This compound is used directly in the next step.

Workup

  1. customThe mixture is degassed for 10 min
  2. filtrationThe reaction mixture is then filtered through celite
  3. extractionaqueous extracted with EtOAc (3×15 mL)
  4. washThe organic is then washed with Brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customHPLC purification

Sources & evidence

ORD record
ord-3cb39c463e9f40cd9f806639112cc780
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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