Triethylamine → N-(2-Fluoro-5-trimethylsilanylethynylbenzyl)-methanesulfonamide

HRID 606815Notes

Reaction equation

C(N(CC)CC)C.Br[C:9]1[CH:10]=[CH:11][C:12]([F:21])=[C:13]([CH:20]=1)[CH2:14][NH:15][S:16]([CH3:19])(=[O:18])=[O:17].[CH3:22][Si:23]([C:26]#[CH:27])([CH3:25])[CH3:24]>O1CCCC1.[Br-].[Zn+2].[Br-].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>[F:21][C:12]1[CH:11]=[CH:10][C:9]([C:27]#[C:26][Si:23]([CH3:25])([CH3:24])[CH3:22])=[CH:20][C:13]=1[CH2:14][NH:15][S:16]([CH3:19])(=[O:18])=[O:17]

Participants

Conditions

Temperature: 60 °C

Procedure

Dissolve zinc (II) bromide (313 mg, 1.20 mmol) in tetrahydrofuran (2.5 mL) and treat with triethylamine (0.64 mL, 4.80 mmol). After 4 min add N-(5-bromo-2-fluorobenzyl)methanesulfonamide (282 mg, 1.00 mmol), (prepared as described in PREPARATION 35), trimethylsilylacetylene (0.30 mL, 2.12 mmol), and tetrakis(triphenylphosphine)palladium (0) (58 mg, 0.050 mmol) to the reddish solution. Heat to 60° C. in a sealed tube overnight, cool to room temperature and filter through diatomaceous earth with ethyl acetate. Concentrate the filtrate and purify the residue by silica gel chromatography, eluting with 75:25 hexanes:ethyl acetate, to give the title compound as a white crystalline solid (220 mg, 74%).

Workup

temperaturecool to room temperature
filtrationfilter through diatomaceous earth with ethyl acetate
concentrationConcentrate the filtrate
custompurify the residue by silica gel chromatography
washeluting with 75:25 hexanes

Sources & evidence

ORD record: ord-d2f92a028c4849448d327706acd8e3fe
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915424B2

Reaction notes

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