Benzo(B)Thiophene-2-Boronic Acid → 5-(2-Benzo[b]thienyl)-3-(1-methylpiperidin-4-yl)-1-(triisopropylsilyl)-indole

HRID 278014Notes

Reaction equation

HRID 278014 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.[S:28]1[C:32](B(O)O)=[CH:31][C:30]2[CH:36]=[CH:37][CH:38]=[CH:39][C:29]1=2.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>[S:28]1[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][C:30]2[CH:36]=[CH:37][CH:38]=[CH:39][C:29]1=2.[S:28]1[C:32]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([Si:11]([CH:12]([CH3:14])[CH3:13])([CH:15]([CH3:16])[CH3:17])[CH:18]([CH3:20])[CH3:19])[CH:6]=[C:5]3[CH:21]2[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]2)=[CH:31][C:30]2[CH:36]=[CH:37][CH:38]=[CH:39][C:29]1=2

Participants

7

Reactant 3

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 10340Sodium CarbonateHCID 120859685-Bromo-3-(1-Methylpiperidin-4-yl)-1-Triisopropylsilylindole

Product 2

HCID 98846285-(Benzo[b]thien-2-yl)-3-(1-Methylpiperidin-4-yl)-1H-IndoleHCID 226268125-(2-Benzo[b]thienyl)-3-(1-methylpiperidin-4-yl)-1-(triisopropylsilyl)-indoleYield 40.8%

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 (0.700 g, 1.56 mmol), benzo[b]thiophene-2-boronic acid (0.336 g, 1.87 mmol), tetrakis(triphenylphosphine)palladium(0) (0.090 g, 0.078 mmol), and 2M aqueous sodium carbonate solution (3 mL) in toluene (15 mL) to give 0.160 g of 5-(2-benzo[b]thienyl)-3-(1-methylpiperidin-4-yl)-1-(triisopropylsilyl)-indole (22%) as a solid, which was desilylated by dissolving in 1 mL of tetrahydrofuran and treating with tetrabutylammonium fluoride (1M in tetrahydrofuran, 7 mL) to give the title compound (0.048 g, 43%) as an amorphous solid. FDMS m/e=346 (M+). EA calculated for C22H22N2S.¼ H2O: C, 75.28; H, 6.46; N, 7.98. Found: C, 75.11; H, 6.84; N, 7.91.

Sources & evidence

ORD record
ord-9d2399faeafc42679852b5a926c327a6
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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