Potassium Phosphate, Tribasic → HCID 131735107, compound

HRID 929236Notes

Reaction equation

HRID 929236 reaction equation
CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C.N1C2C(=CC=CC=2)CC1.FC(F)(F)C(O)=O.[N:50]1[N:51]([CH2:58][C:59]([CH3:62])([OH:61])[CH3:60])[CH:52]=[C:53]2[CH2:57][NH:56][CH2:55][C:54]=12.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:71]([N:74]1[C:82]2[C:77](=[N:78][C:79](I)=[C:80]([Cl:83])[CH:81]=2)[N:76]=[C:75]1[O:85][C@@H:86]1[CH2:90][O:89][C@@H:88]2[C@H:91]([O:94][Si:95]([C:98]([CH3:101])([CH3:100])[CH3:99])([CH3:97])[CH3:96])[CH2:92][O:93][C@H:87]12)[CH:72]=[CH2:73]>O1CCOCC1>[Si:95]([O:94][C@H:91]1[C@H:88]2[O:89][CH2:90][C@@H:86]([O:85][C:75]3[N:74]([CH2:71][CH:72]=[CH2:73])[C:82]4[C:77]([N:76]=3)=[N:78][C:79]([N:56]3[CH2:57][C:53]5[C:54](=[N:50][N:51]([CH2:58][C:59]([CH3:62])([OH:61])[CH3:60])[CH:52]=5)[CH2:55]3)=[C:80]([Cl:83])[CH:81]=4)[C@H:87]2[O:93][CH2:92]1)([C:98]([CH3:100])([CH3:101])[CH3:99])([CH3:96])[CH3:97]

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 123197088HCID 123197088, compoundHCID 131735108HCID 131735108, compoundHCID 131735109HCID 131735109, compound

Product 1

HCID 131735107HCID 131735107, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of Ruphos indoline precatalyst (12.6 mg, 0.017 mmol, Strem), 1-(5,6-dihydro-4H-pyrrolo[3,4-c]pyrazol-2-yl)-2-methyl-propan-2-ol 2,2,2-trifluoroacetic acid (102 mg, 0.346 mmol), potassium phosphate tribasic (184 mg, 0.865 mmol) and [(3R,3aR,6R,6aS)-3-(1-allyl-6-chloro-5-iodo-imidazo[4,5-b]pyridin-2-yl)oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]oxy-tert-butyl-dimethyl-silane (100 mg, 0.173 mmol) in dioxane (1.0 ml) was degassed (3×) and placed under nitrogen before being heated to 110° C. After 18 hours, the reaction mixture was cooled to room temperature, diluted with EtOAc (30 ml), washed with water (20 ml), brine (10 mL), dried over MgSO4, filtered, and evaporated under reduced pressure to give an oil. The oil was purified on preparative silica plates (1×1000 u developed and eluted with EtOAc) to give the title compound. LC-MS: calculated for C30H43ClN6O5Si 630.28 observed m/e: 631.27 (M+H)+ (Rt 1.36/2 min)

Workup

  1. customwas degassed (3×)
  2. temperaturethe reaction mixture was cooled to room temperature
  3. additiondiluted with EtOAc (30 ml)
  4. washwashed with water (20 ml), brine (10 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto give an oil
  9. customThe oil was purified on preparative silica plates (1×1000 u developed and eluted with EtOAc)

Sources & evidence

ORD record
ord-310ea8af630c4c9f981052e5968faa7d
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

Loading…