Sodium Carbonate → 5-(4-chlorophenyl)-3-(1-methylpiperidin-4-yl)-1H-indole

HRID 278012Notes

Reaction equation

HRID 278012 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([Si](C(C)C)(C(C)C)C(C)C)[CH:6]=[C:5]2[CH:21]1[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[C:5]3[CH:21]2[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]2)=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 120859685-Bromo-3-(1-Methylpiperidin-4-yl)-1-Triisopropylsilylindole

Product 1

HCID 98620775-(4-chlorophenyl)-3-(1-methylpiperidin-4-yl)-1H-indole

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

The title compound was prepared by the procedure of Example 10, beginning with 5-bromo-3-(1-methylpiperidin-4-yl)-1-(triisopropylsilyl)-indole (0.500 g, 1.11 mmol), 4-chlorophenylboronic acid (0.183 g, 1.17 mmol), tetrakis(triphenylphosphine)palladium(0) (0.064 g, 0.056 mmol), and 2M aqueous sodium carbonate solution (2 mL) in toluene (15 mL) to give 0.200 g of 5-(4-chlorophenyl)-3-(1-nethylpiperidin-4-yl)-1-(triisopropylsilyl)-indole (40%) as a white solid, which was desilylated by dissolving in 1 mL of tetrahydrofuran and treating with tetrabutylammonium fluoride (1M in tetrahydrofuran, 4 mL) to give the title compound (0.112 g, 83%) as an amorphous solid. FDMS m/e=325 (M+). EA calculated for C20H21N2Cl.½ H2O: C, 71.95; H, 6.64; N, 8.39. Found: C, 72.09; H, 6.68; N, 8.48.

Sources & evidence

ORD record
ord-018adce6465740a0aa28982392d07194
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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