Dimethylacetamide → HCID 71127341, compound

HRID 1912105Notes

Reaction equation

HRID 1912105 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH:21]([C:30]1[N:31]=[N:32][N:33]([CH:36]2[CH2:39][CH:38]([CH2:40][CH:41]([CH3:43])[CH3:42])[CH2:37]2)[C:34]=1I)[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:44]1(B2OC(C)(C)C(C)(C)O2)[CH2:46][CH2:45]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN(C)C(=O)C>O>[Si:1]([O:18][CH2:19][CH2:20][CH:21]([C:30]1[N:31]=[N:32][N:33]([CH:36]2[CH2:39][CH:38]([CH2:40][CH:41]([CH3:43])[CH3:42])[CH2:37]2)[C:34]=1[CH:44]1[CH2:46][CH2:45]1)[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 31374DimethylacetamideHCID 62657Potassium Phosphate, TribasicHCID 27580152-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 71127340HCID 71127340, compound

Product 1

HCID 71127341HCID 71127341, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-[5-iodo-1-(3-isobutylcyclobutyl)-1H-[1,2,3]triazol-4-yl]valerate (340 mg), 2-cyclopropyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (0.16 mL), tripotassium phosphate (403 mg), N,N-dimethylacetamide (3.4 mL) and water (0.85 mL) were mixed. The mixture was degassed by bubbling argon gas. To the mixture was added PdCl2(PPh3)2 (50 mg). The mixture was stirred at 80° C. for 1 hr. To the reaction mixture was added ethyl acetate at ice temperature, and then the mixture was filtered. The filtrate was washed with water and brine, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/20) to give the title compound (238 mg).

Workup

  1. customThe mixture was degassed
  2. customby bubbling argon gas
  3. additionTo the mixture was added PdCl2(PPh3)2 (50 mg)
  4. additionTo the reaction mixture was added ethyl acetate at ice temperature
  5. filtrationthe mixture was filtered
  6. washThe filtrate was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe magnesium sulfate was filtered off
  9. concentrationthe filtrate was concentrated in vacuo
  10. customThe resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/20)

Sources & evidence

ORD record
ord-a6fc6f765a224a979d172f3bbb4933c7
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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