HCID 67427392, compound → HCID 67428369, compound

HRID 1509351Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4](/[CH:7]=[CH:8]/[C:9]2[S:10][CH:11]=[C:12](Br)[CH:13]=2)[S:5][CH:6]=1.[CH2:15]([Mg]Br)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:15]([C:2]1[CH:3]=[C:4](/[CH:7]=[CH:8]/[C:9]2[S:10][CH:11]=[C:12]([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15])[CH:13]=2)[S:5][CH:6]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 16 (1.1 g, 3.14 mmol) and NiCl2(dppp) (0.17 g, 0.31 mmol) was degassed in a 2 necked RBF. Anhydrous THF (25 mL) was then added to the mixture. C12H25MgBr (1M in THF, 8 mL, 8 mmol) was added dropwise to the reaction mixture and heated at 60° C. overnight. The reaction was quenched with 2N aqueous HCl, extracted with CH2Cl2 and filtered through celite. The residue was purified by column chromatography (silica gel, hexane/CH2Cl2, 4:1) and recrystallized from hexane to give a yellow solid compound 17 in 38% yield. 1H-NMR (DCM-d2, 400 MHz) ppm 0.88 (t, 6H, J=6.8 Hz) ppm 1.29 (m, 36H) ppm 1.60 (td, 4H, J=7.2 Hz, J=14.6 Hz) ppm 2.55 (m, 4H) ppm 6.78 (s, 2H) ppm 6.88 (s, 2H) ppm 6.96 (s, 2H).

Workup

customwas degassed in a 2 necked RBF
additionAnhydrous THF (25 mL) was then added to the mixture
customThe reaction was quenched with 2N aqueous HCl
extractionextracted with CH2Cl2
filtrationfiltered through celite
customThe residue was purified by column chromatography (silica gel, hexane/CH2Cl2, 4:1)
customrecrystallized from hexane

Sources & evidence

ORD record: ord-8587c952e1e743efbf11bf19617d07bb
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221944B2

Reaction notes

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