Potassium Phosphate, Tribasic → HCID 89590857, compound

HRID 522416Notes

Reaction equation

HRID 522416 reaction equation
[C:1]([C@H:5]1[C:39](=[O:40])[N:38]2[CH2:41][C@@H:35]([CH2:36][C@H:37]2[C:42]([O:44][CH3:45])=[O:43])[O:34][C:17]2=[N:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25](OS(C(F)(F)F)(=O)=O)=[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[CH2:46][C@H:9]2[O:8][C:7](=[O:47])[NH:6]1)([CH3:4])([CH3:3])[CH3:2].[N:48]1[CH:53]=[CH:52][C:51](B(O)O)=[CH:50][CH:49]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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>[C:1]([C@H:5]1[C:39](=[O:40])[N:38]2[CH2:41][C@@H:35]([CH2:36][C@H:37]2[C:42]([O:44][CH3:45])=[O:43])[O:34][C:17]2=[N:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25]([C:51]3[CH:52]=[CH:53][N:48]=[CH:49][CH:50]=3)=[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[CH2:46][C@H:9]2[O:8][C:7](=[O:47])[NH:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2734379(Pyridin-4-yl)boronic acidHCID 89590960HCID 89590960, compound

Product 1

HCID 89590857HCID 89590857, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the product from step 1 (50 mg, 0.073 mmol) in dioxane (5 ml) was added pyridine-4-boronic acid, (35.9 mg, 0.292 mmol), potassium phosphate tribasic (38.7 mg, 0.182 mmol) and tetrakis (16.85 mg, 0.015 mmol). After purging with N2 for 5 min, the reaction was stirred at 80° C. for 16 hours. After cooling to room temperature, water was added and the reaction was extracted with ethyl acetate, washed with brine, dried (Na2SO4) and concentrated. Purification by PTLC (40% EtOAc/hexane) provided the desired compound.

Workup

  1. customAfter purging with N2 for 5 min
  2. temperatureAfter cooling to room temperature
  3. additionwater was added
  4. extractionthe reaction was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customPurification by PTLC (40% EtOAc/hexane)

Sources & evidence

ORD record
ord-1ed6d787100e40e5813c3e862ca28d46
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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