Potassium Phosphate, Tribasic → HCID 71765338, compound

HRID 1399989Notes

Reaction equation

HRID 1399989 reaction equation
Br[C:2]1[C:3]([O:17][CH2:18][CH:19]2[CH2:23][CH2:22][CH2:21][O:20]2)=[CH:4][C:5]2[S:9][C:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])=[N:7][C:6]=2[CH:16]=1.C(NC(NC1SC2C(C3C=CC=CN=3)=CC([C:45]3[CH:46]=[N:47][C:48]([C:51]([OH:54])([CH3:53])[CH3:52])=[N:49][CH:50]=3)=CC=2N=1)=O)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:14]([NH:13][C:11]([NH:10][C:8]1[S:9][C:5]2[CH:4]=[C:3]([O:17][CH2:18][CH:19]3[CH2:23][CH2:22][CH2:21][O:20]3)[C:2]([C:45]3[CH:46]=[N:47][C:48]([C:51]([OH:54])([CH3:53])[CH3:52])=[N:49][CH:50]=3)=[CH:16][C:6]=2[N:7]=1)=[O:12])[CH3:15]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 71726538HCID 71726538, compoundHCID 86696900HCID 86696900, compound

Product 1

HCID 71765338HCID 71765338, compoundYield 43.7%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 21966525Dioxane MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of iv (0.303 g, 0.75 mmol) and the 4,4,5,5-tetramethyl-1,3,2-dioxaborolon-2-yl) ester of Precursor 1 (0.20 g, 0.75 mmol) in 1,4-dioxane:MeOH (5:3, 8.0 mL) was added potassium phosphate (0.24 g, 1.13 mmol) at RT. The mixture was degassed for 15-20 min by purging N2 followed by the addition of Pd(dppf)Cl2 (0.062 g, 0.075 mmol). The mixture was degassed for 15-20 min and heated at 80° C. for 5 h. The reaction mixture was cooled to RT, diluted with EtOAc (500 ml) and filtered through celite. The filtrate was evaporated in vacuo and the crude residue was purified over silica (5% MeOH-DCM) to obtain Compound 3 (0.15 g, 43%).

Workup

  1. customThe mixture was degassed for 15-20 min
  2. customby purging N2
  3. customThe mixture was degassed for 15-20 min
  4. temperatureThe reaction mixture was cooled to RT
  5. additiondiluted with EtOAc (500 ml)
  6. filtrationfiltered through celite
  7. customThe filtrate was evaporated in vacuo
  8. customthe crude residue was purified over silica (5% MeOH-DCM)

Sources & evidence

ORD record
ord-fd47708c498a4ecc92c0107b60c775a5
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

Loading…