Potassium Phosphate, Tribasic → HCID 68433767, compound

HRID 1713947Notes

Reaction equation

HRID 1713947 reaction equation
Br[C:2]1[N:3]([CH2:21][C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2.[CH:27]1(B(O)O)[CH2:29][CH2:28]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].CCOC(C)=O>[CH:11]1([C:10]2[C:9]3[C:4](=[CH:5][C:6]([C:17]([O:19][CH3:20])=[O:18])=[CH:7][CH:8]=3)[N:3]([CH2:21][C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[C:2]=2[CH:27]2[CH2:29][CH2:28]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 21105286HCID 21105286, compound

Product 1

HCID 68433767HCID 68433767, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 2-bromo-3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-1H-indole-6-carboxylate (prepared as in published International patent application WO2004/087714) in toluene (0.24 M) was added cyclopropylboronic acid (1.3 eq.) followed by potassium phosphate (3.5 eq.). The mixture was degassed, then Pd(OAc)2 (0.1 eq.) and tricyclohexylphosphine (0.2 eq.) were added. The reaction was stirred under nitrogen at 100° C. for 1.5 h and then cooled to RT. EtOAc was added and the organic phase was washed with water and brine, dried over NaSO4 and evaporated in vacuo to leave a residue which was purified by flash chromatography (PE/EtOAc 1/1) to give the title compound (70%).

Workup

  1. customThe mixture was degassed
  2. temperaturecooled to RT
  3. washthe organic phase was washed with water and brine
  4. dry with materialdried over NaSO4
  5. customevaporated in vacuo
  6. customto leave a residue which
  7. customwas purified by flash chromatography (PE/EtOAc 1/1)

Sources & evidence

ORD record
ord-50a40cc2bf8c4665b6abde1dbc40559d
Source dataset
uspto-grants-2010_09
Patent number
US07795250B2

Reaction notes

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