Trimethylsilylacetylene → HCID 86701678, compound

HRID 2174056Notes

Reaction equation

HRID 2174056 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:22])[C:5](I)=[C:6]2[C:10]=1[N:9]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2.[CH3:23][Si:24]([C:27]#[CH:28])([CH3:26])[CH3:25]>C(N(CC)CC)C.[Cu]I.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>[Br:1][C:2]1[CH:3]=[C:4]([CH3:22])[C:5]([C:28]#[C:27][Si:24]([CH3:26])([CH3:25])[CH3:23])=[C:6]2[C:10]=1[N:9]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:8]=[CH:7]2

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 86701679HCID 86701679, compound

Product 1

HCID 86701678HCID 86701678, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

To a suspension of 7-bromo-4-iodo-5-methyl-1-tosyl-1H-indole (90 mg, 0.184 mmol), CuI (5.60 mg, 0.029 mmol) and Pd(PPh3)4 (16.9 mg, 0.015 mmol) in triethylamine (3 mL) was added trimethylsilylacetylene (0.036 mL, 0.257 mmol) and the mixture was stirred at room temperature. After 3 hours the reaction was purified directly by flash chromatography (0-40% EtOAc in heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.03 (d, J=3.79 Hz, 1H) 7.70 (d, J=8.34 Hz, 2H) 7.34-7.48 (m, 3H) 6.85 (d, J=3.79 Hz, 1H) 2.38 (s, 3H) 2.37 (s, 3H) 0.27-0.31 (m, 9H).

Workup

  1. customAfter 3 hours the reaction was purified directly by flash chromatography (0-40% EtOAc in heptanes)

Sources & evidence

ORD record
ord-e801d92c2653417f932bb2b957d87442
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

Loading…