Sodium Carbonate → 5-(4-Methoxyphenyl)-3-(1-methylpiperidin-4-yl)-1-(triisopropylsilyl)-indole

HRID 278013Notes

Reaction equation

HRID 278013 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:6]=[C:5]2[CH:21]1[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]1.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=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>[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([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:32][CH:31]=1.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([Si:11]([CH:18]([CH3:19])[CH3:20])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:13])[CH3:14])[CH:6]=[C:5]3[CH:21]2[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]2)=[CH:32][CH:31]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 120859685-Bromo-3-(1-Methylpiperidin-4-yl)-1-Triisopropylsilylindole

Product 2

HCID 98618905-(4-methoxyphenyl)-3-(1-methylpiperidin-4-yl)-1H-indoleHCID 226268015-(4-Methoxyphenyl)-3-(1-methylpiperidin-4-yl)-1-(triisopropylsilyl)-indoleYield 47%

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 (0.600 g, 1.34 mmol), 4-methoxyphenylboronic acid (0.213g, 1.40 mmol), tetrakis(triphenylphosphine)palladium(0) (0.077g, 0.067 mmol), and 2M aqueous sodium carbonate solution (2 mL) in toluene (15 mL) to give 0.150 g of 5-(4-methoxyphenyl)-3-(1-methylpiperidin-4-yl)-1-(triisopropylsilyl)-indole (24%) as a 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 (0.050 g, 45%) as an amorphous solid. FDMS m/e 320 (M+). EA calculated for C21H24N2O.⅛ H2O: C, 78.17; H, 7.57; N, 8.68. Found: C, 78.13; H, 7.92; H, 8.43.

Sources & evidence

ORD record
ord-640e4ff9aa8f473b8ef3ad6cce10583f
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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