Potassium Carbonate → HCID 73336182, compound

HRID 925788Notes

Reaction equation

HRID 925788 reaction equation
[F:1][C:2]1[CH:10]=[C:9](B2OC(C)(C)C(C)(C)O2)[C:8]2[N:7]3[CH2:20][CH2:21][NH:22][C:23](=[O:24])[C:6]3=[C:5]([CH3:25])[C:4]=2[CH:3]=1.Br[C:27]1[S:28][CH:29]=[CH:30][N:31]=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:10]=[C:9]([C:27]2[S:28][CH:29]=[CH:30][N:31]=2)[C:8]2[N:7]3[CH2:20][CH2:21][NH:22][C:23](=[O:24])[C:6]3=[C:5]([CH3:25])[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 764302-BromothiazoleHCID 90036316HCID 90036316, compound

Product 1

HCID 73336182HCID 73336182, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 8-fluoro-10-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (Step A) (48 mg, 139 μmol) and 2-bromothiazole (34.3 mg, 18.6 μl, 209 μmol) in 1,2-dimethoxyethane (1 ml), 2M potassium carbonate solution (232 μl, 464 μmol) was added and the reaction mixture purged with argon in an ultrasonic bath during 5 min. Then triphenylphosphine (7.32 mg, 27.9 μmol) and palladium(II)acetate (3.13 mg, 13.9 μmol) were added and the reaction mixture was allowed to stir for 3 h under reflux conditions. The reaction mixture was cooled to room temperature, filtered (MgSO4) and purified by flash chromatography on silica gel [dichloro methane/methanol (0-5%)] and subsequent trituration (diethyl ether) to yield the title compound as a light brown solid (6 mg, 15%), MS (ISP) m/z=302.5 [(M+H)+], mp 268° C.

Workup

  1. additionwas added
  2. customthe reaction mixture purged with argon in an ultrasonic bath during 5 min
  3. filtrationfiltered (MgSO4)
  4. custompurified by flash chromatography on silica gel [dichloro methane/methanol (0-5%)] and subsequent trituration (diethyl ether)

Sources & evidence

ORD record
ord-ac720c762021429586c9685a954e13bc
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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