Sodium Carbonate → 2-(6-chloro-5-methyl-2-(triethylsilyl)-1H-indol-3-yl)ethanol

HRID 1777547Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5](I)=[C:6]([CH:8]=1)[NH2:7].[CH2:11]([Si:13]([CH2:21][CH3:22])([CH2:19][CH3:20])[C:14]#[C:15][CH2:16][CH2:17][OH:18])[CH3:12].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd](Cl)Cl>[Cl:1][C:2]1[CH:8]=[C:6]2[C:5]([C:15]([CH2:16][CH2:17][OH:18])=[C:14]([Si:13]([CH2:19][CH3:20])([CH2:21][CH3:22])[CH2:11][CH3:12])[NH:7]2)=[CH:4][C:3]=1[CH3:10]

Participants

Conditions

Temperature: 100 °C

Procedure

5-Chloro-2-iodo-4-methylaniline (1.50 g; 5.61 mmol), 4-(triethylsilyl)but-3-yn-1-ol (2.36 mL; 11.22 mmol), bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.229 g; 0.280 mmol), lithium chloride (0.237 g; 5.61 mmol) and sodium carbonate (1.19 g; 11.22 mmol) were suspended in DMF (14 mL) and the mixture was stirred at 100° C. for 15 hours. The solution was concentrated under reduced pressure and diluted in ethyl acetate. The organic layer was successively washed with brine, sodium thiosulfate, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford 1.44 g (79%) of the title compound as a brown oil.

Workup

concentrationThe solution was concentrated under reduced pressure
additiondiluted in ethyl acetate
washThe organic layer was successively washed with brine, sodium thiosulfate
customdried
concentrationconcentrated under reduced pressure
customThe crude residue was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-ee49a50d6c294683bf745121c4d41c47
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266832B2

Reaction notes

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