Potassium Phosphate, Tribasic → HCID 66906357, compound

HRID 1689776Notes

Reaction equation

HRID 1689776 reaction equation
[C:1]([Si:5]([CH3:23])([CH3:22])[O:6][CH:7]1[CH2:12][CH2:11][C:10](B2OC(C)(C)C(C)(C)O2)=[CH:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[CH3:24][O:25][C:26]([C:28]1[C:36]2[C:31](=[CH:32][C:33](Br)=[CH:34][CH:35]=2)[N:30]([CH3:38])[CH:29]=1)=[O:27].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[CH3:24][O:25][C:26]([C:28]1[C:36]2[C:31](=[CH:32][C:33]([C:10]3[CH2:11][CH2:12][CH:7]([O:6][Si:5]([C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:22])[CH3:23])[CH2:8][CH:9]=3)=[CH:34][CH:35]=2)[N:30]([CH3:38])[CH:29]=1)=[O:27]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 53393368Tert-butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)oxy)silaneHCID 57443279Methyl 6-bromo-1-methyl-1H-indole-3-carboxylate

Product 1

HCID 66906357HCID 66906357, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A flask containing a solution of 2-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (1.40 g, 4.14 mmol) and 6-bromo-1-methyl-1H-indole-3-carboxylic acid methyl ester (1.22 g, 4.55 mmol) in toluene (50 mL) is evacuated and filled with N2 three times. Potassium phosphate (1.79 g, 8.27 mmol), Pd(OAc)2 (46 mg), and 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (S-Phos, 50 mg) are added. The mixture is stirred at 100° C. for 16 h and cooled to room temperature. The mixture is filtered through a pad of diatomaceous earth, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel chromatography eluting with 25% EtOAc/Hexanes to provide the title compound (0.71 g, 43%). MS m/z 400.3 (M+1).

Workup

  1. customis evacuated
  2. additionfilled with N2 three times
  3. temperaturecooled to room temperature
  4. filtrationThe mixture is filtered through a pad of diatomaceous earth
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. customThe residue is purified by silica gel chromatography
  7. washeluting with 25% EtOAc/Hexanes

Sources & evidence

ORD record
ord-fc3ec5748ba546eba714352e89f9c077
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

Loading…