Heptadecylamine → HCID 67247093, compound

HRID 2410244Notes

Reaction equation

HRID 2410244 reaction equation
Br[C:2]1(Br)[CH:6]=[CH:5][S:4][CH:3]1[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1.C(O[Na])(C)(C)C.C1C=CC(P([C:32]2[C:41]([C:42]3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=C[CH:49]=[C:48]4[C:43]=3[CH:44]=[CH:45][CH:46]=[CH:47]4)=C3[C:35]([CH:36]=[CH:37][CH:38]=[CH:39]3)=[CH:34][CH:33]=2)C2C=CC=CC=2)=CC=1.C(CCCCCCCCC[NH2:82])CCCCCCC>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH2:32]([CH:41]([N:82]1[C:11]2[CH:10]=[CH:9][S:8][C:7]=2[C:3]2[S:4][CH:5]=[CH:6][C:2]1=2)[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

8

Reactant 4

HCID 15791HeptadecylamineHCID 634876Binap, (A+-)-HCID 67246593HCID 67246593, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 67247093HCID 67247093, compoundYield 813.6%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 3,3-dibromo-2,2′-bithiophene (4.92 g, 15.3 mmol), t-BuONa (3.54 g, 36.8 mmol), Pd2 dba3 (0.35 g, 0.382 mmol) and BINAP (0.95 g, 1.53 mmol) in toluene (38 mL) under an argon atmosphere was added 9-octylnonylamine (4 g, 15.7 mmol). The reaction mixture was subsequently stirred at 110° C. over a period of 7 hours. The reaction mixture was allowed to cool to room temperature followed by the addition of water. The organic layer was removed and the remaining aqueous phase extracted several times with diethyl ether. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated. Purification by column chromatography using hexanes as the eluant afforded the title compound as a light green solid (5.2 g, 81% yield): mp: 60° C.; GC-Ms: 417.5; 1H NMR (400 MHz, CDCl3, ppm) δ: 7.11(d, 2H), 7.02-7.01(d, 2H), 4.23-4.19(m, 1H), 2.08(m, 2H), 1.85-1.80(m, 2H), 1.22-1.07(m, 24 H), 0.86-0.82(t, 6 H); 13C NMR (100 MHz, CDCl3, ppm) δ: 144.2, 122, 4, 114.9, 59.9, 35.4, 31.9, 29.4, 29.3, 26.7, 22.8, 14.2.

Workup

  1. temperatureto cool to room temperature
  2. customThe organic layer was removed
  3. extractionthe remaining aqueous phase extracted several times with diethyl ether
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-8823fb03b7be4ed092c73f430ecb546c
Source dataset
uspto-grants-2014_08
Patent number
US08816035B2

Reaction notes

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