(6-Bromohexyl)benzene → HCID 24951316, compound

HRID 877408Notes

Reaction equation

HRID 877408 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Li]C(C)(C)C.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[S:29][C:28]([C:30](OC)=[O:31])=[N:27][N:26]=1>C1COCC1>[C:8]1([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:30]([C:28]2[S:29][C:25]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=3)=[N:26][N:27]=2)=[O:31])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 561788(6-Bromohexyl)benzeneHCID 58366192HCID 58366192, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 24951316HCID 24951316, compoundYield 7.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-bromohexylbenzene (31 pt, 0.2 mmol) in THF (1 mL) was treated dropwise with 1.7 M t-BuLi (235 μL, 0.4 mmol) at −78° C. After stirring for 30 min, the resulting alkyllithium reagent was added to a cooled solution of methyl 5-(pyridin-2-yl)-1,3,4-thiadiazole-2-carboxylate (S43, 44 mg, 0.2 mmol) in THF (0.5 mL) at −78° C. The reaction mixture was stirred for 3 h at −78° C. before it was quenched with the addition of MeOH. The mixture was extracted with EtOAc, washed with water, saturated aqueous NaHCO3 and saturated aqueous NaCl, and dried over Na2SO4. Evaporation in vacuo yielded the crude product which was purified by flash chromatography (SiO2, 3×14 cm, 15% EtOAc-hexanes) to provide the title compound (5.1 mg, 7%) as white solid: 1H NMR (CDCl3, 600 MHz) δ 8.69 (m, 1H), 8.41 (dd, 1H, J=0.8, 7.9 Hz), 7.89 (m, 1H), 7.45 (m, 1H), 7.27 (m, 2H), 7.17 (m, 3H), 3.27 (t, 2H, J=7.4 Hz) 2.61 (t, 2H, J=7.7 Hz), 1.81 (m, 2H), 1.65 (m, 2H), 1.45 (m, 4H); 13C NMR (CDCl3, 150 MHz) δ 194.1, 174.9, 169.6, 150.3, 148.6, 142.8, 137.5, 128.5, 128.4, 126.3, 125.7, 121.7, 39.4, 36.0, 31.4, 29.9, 29.1, 24.0; IR (film) νmax 2927, 2854, 1734, 1685, 1647, 1584, 1406, 1009, 785, 742, 698 cm−1; HRMS-ESI-TOF m/z 352.1474 ([M+H]+, C20H21N3OS requires 352.1478).

Workup

  1. stirringThe reaction mixture was stirred for 3 h at −78° C. before it
  2. customwas quenched with the addition of MeOH
  3. extractionThe mixture was extracted with EtOAc
  4. washwashed with water, saturated aqueous NaHCO3 and saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. customEvaporation in vacuo
  7. customyielded the crude product which
  8. customwas purified by flash chromatography (SiO2, 3×14 cm, 15% EtOAc-hexanes)

Sources & evidence

ORD record
ord-f4b3bd38db654b44bcd1f785e2919fa2
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

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