Sodium Carbonate → 2-(2-(triethylsilyl)-5-(trifluoromethyl)-1H-indol-3-yl)ethanol

HRID 1918614Notes

Reaction equation

I[C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:13]([Si:15]([CH2:23][CH3:24])([CH2:21][CH3:22])[C:16]#[C:17][CH2:18][CH2:19][OH:20])[CH3:14].[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>[CH2:23]([Si:15]([CH2:13][CH3:14])([CH2:21][CH3:22])[C:16]1[NH:4][C:3]2[C:2]([C:17]=1[CH2:18][CH2:19][OH:20])=[CH:8][C:7]([C:9]([F:12])([F:11])[F:10])=[CH:6][CH:5]=2)[CH3:24]

Participants

Conditions

Temperature: 100 °C

Procedure

2-iodo-4-(trifluoromethyl)aniline (1.0 g; 3.48 mmol), 4-(triethylsilyl)but-3-yn-1-ol (0.807 mL; 3.83 mmol), Bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.142 g; 0.174 mmol), lithium chloride (0.147 g; 3.48 mmol) and sodium carbonate (0.738 g; 6.97 mmol) were suspended in DMF (10 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 thiosulphate, dried and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane) to afford 0.733 g (61%) of the title compound as a yellow oil.

Workup

concentrationThe solution was concentrated under reduced pressure
additiondiluted in ethyl acetate
washThe organic layer was successively washed with brine, sodium thiosulphate
customdried
concentrationconcentrated under reduced pressure
customThe crude material was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-18e1c08b980749c4a0d207d57c3c29de
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618138B2

Reaction notes

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