Potassium Phosphate, Tribasic → HCID 89524899, compound

HRID 706347Notes

Reaction equation

HRID 706347 reaction equation
CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC1(C)C(C)(C)OB([C:51]2[CH:65]=[CH:64][CH:63]=[CH:62][C:52]=2[CH2:53][NH:54][C:55](=[O:61])[O:56][C:57]([CH3:60])([CH3:59])[CH3:58])O1.[I:67][C:68]1[O:69][CH:70]=[C:71](I)[N:72]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[I:67][C:68]1[O:69][CH:70]=[C:71]([C:51]2[CH:65]=[CH:64][CH:63]=[CH:62][C:52]=2[CH2:53][NH:54][C:55](=[O:61])[O:56][C:57]([CH3:58])([CH3:59])[CH3:60])[N:72]=1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 249996922,4-Diiodo-1,3-oxazoleHCID 56776828tert-Butyl {[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}carbamate

Product 1

HCID 89524899HCID 89524899, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

Palladium(II) acetate (35.0 mg, 0.156 mmol) and Xantphos (90 mg, 0.156 mmol) was added to degassed THF (3 ml) and let stir for 5 minutes then transferred to a separate rxn vessel that contained tert-butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate (1142 mg, 3.43 mmol), 2,4-diiodooxazole (1000 mg, 3.12 mmol), Potassium phosphate (1985 mg, 9.35 mmol) and degassed Tetrahydrofuran (THF) (12 mL). The rxn vessel was capped and heated to 80° for 16 hours. Filtered and the residue was purified via Biotage (0% to 100% DCM:Hex; 50 g-HP-silica gel column) to obtain 460 mg of tert-butyl 2-(2-iodooxazol-4-yl)benzylcarbamate. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.47 (s, 9H) 4.39 (d, J=5.31 Hz, 2H) 5.40 (br. s., 1H) 7.31-7.45 (m, 2H) 7.53 (dd, J=19.45, 7.07 Hz, 2H) 7.94 (s, 1H); MS[MH]+=401.1

Workup

  1. customto degassed THF (3 ml)
  2. customthen transferred to a separate rxn vessel
  3. customdegassed Tetrahydrofuran (THF) (12 mL)
  4. customThe rxn vessel was capped
  5. temperatureheated to 80° for 16 hours
  6. filtrationFiltered
  7. customthe residue was purified via Biotage (0% to 100% DCM:Hex; 50 g-HP-silica gel column)

Sources & evidence

ORD record
ord-bec631d9396a48a1883eb06d86e8d5c1
Source dataset
uspto-grants-2015_11
Patent number
US09174984B2

Reaction notes

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