Potassium Phosphate, Tribasic → HCID 118114057, compound

HRID 706521Notes

Reaction equation

HRID 706521 reaction equation
C(OC(=O)[NH:5][C:6]1[N:15]([CH:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]3[CH:27]=[N:28][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:31]=3)=[C:20]([O:36][CH3:37])[CH:19]=2)[CH3:17])[C:9]2=[N:10][CH:11]=[C:12]([I:14])[CH:13]=[C:8]2[N:7]=1)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(O)C.O>[I:14][C:12]1[CH:13]=[C:8]2[N:7]=[C:6]([NH2:5])[N:15]([CH:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]4[CH:27]=[N:28][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:30][CH:31]=4)=[C:20]([O:36][CH3:37])[CH:19]=3)[CH3:17])[C:9]2=[N:10][CH:11]=1

Participants

5

Reactant 2

HCID 62657Potassium Phosphate, TribasicHCID 131733702HCID 131733702, compound

Product 1

HCID 118114057HCID 118114057, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
160 °C

Procedure

To a stirred solution of ethyl(6-iodo-3-(1-(3-methoxy-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)phenyl)ethyl)-3H-imidazo[4,5-b]pyridin-2-yl)carbamate (1.53 g, 2.39 mmol), in ethanol (10 mL)/water (4 mL) was added potassium phosphate tribasic (2.07 g, 9.54 mmol). The mixture was irradiated in a microwave reactor at 150° C. After 1 h, the mixture was subjected to an additional round of microwave heating (160° C., 30 min). After a total of 90 min, the mixture was diluted with water (100 mL) and extracted with dichloromethane (2×50 mL). The combined organic phases were dried over magnesium sulfate, filtered, and concentrated to provide 1.31 g (97%) of 6-iodo-3-(1-(3-methoxy-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)phenyl)ethyl)-3H-imidazo[4,5-b]pyridin-2-amine as an orange foamy solid.

Workup

  1. customThe mixture was irradiated in a microwave reactor at 150° C
  2. extractionextracted with dichloromethane (2×50 mL)
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ff9a54608714446598b8310419914bce
Source dataset
uspto-grants-2015_11
Patent number
US09174986B2

Reaction notes

Loading…