11-Mercapto-1-undecanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Five (5) mg of the oleic acid-stabilized CdSe quantum dots and 50 mg of 1-mercapto-1-undecanol were mixed with 5 ml of chloroform and 5 ml of ethanol. The mixture was then sonicated for 3 hours. Then, 40 ml of chloroform was added to the mixture to obtain a precipitate of 11-mercapto-1-undecanol capped CdSe quantum dots. The precipitate was dissolved in ethanol and dimethyl sulfoxide (“DMSO”). The mixture was then sonicated for 3 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Five (5) mg of the oleic acid-stabilized CdSe quantum dots and 50 mg of 1-mercapto-1-undecanol were mixed with 5 ml of chloroform and 5 ml of ethanol. The mixture was then sonicated for 3 hours. Then, 40 ml of chloroform was added to the mixture to obtain a precipitate of 11-mercapto-1-undecanol capped CdSe quantum dots. The precipitate was dissolved in ethanol and dimethyl sulfoxide (“DMSO”). The mixture was then sonicated for 3 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was synthesized in a manner analogous to that described in Org. Lett. 2004, 6(24), 4587-4590. To a round bottom flask were added 6-iodo-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide (1.0 g, 2.31 mmol), dry dioxane (23 mL) and i-Pr2NEt (0.81 mL, 4.62 mmol). Catalytic Pd2(dba)3 (63 mg, 0.07 mmol), Xantphos (80 mg, 0.14 mmol) and 11-mercapto-1-undecanol (494 mg, 2.42 mmol) were then added. The mixture was evacuated and backfilled with nitrogen (3 cycles). The mixture was heated to reflux for 2 h (HPLC confirmed the completion of the reaction). The reaction mixture was then allowed to reach ambient temperature followed by filtration and concentration. The crude product was used without further purification for the next step. ES/MS calcd. for C29H40N3O3S+ 510.3. Found m/z=510.4 (M+H)+. The mixture was evacuated The mixture was heated to reflux for 2 h (HPLC the completion of the reaction) to reach ambient temperature followed by filtration and concentration The crude product was used without further purification for the next step

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Mercaptoundecyl bromoisobutyrate was synthesized through the reaction of bromoisobutyryl bromide and 11-mercapto-1-undecanol using a method published previously. 1H NMR (300 MHz, CDCl3): 4.15 (t, J=6.9 Hz, 2H, OCH2), 2.51 (q, J=7.5 Hz, 2H, SCH2), 1.92 (s, 6H, CH3), 1.57-1.72 (m, 4H, CH2), and 1.24-1.40 (m, 16H, CH2).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 11-Mercaptoundecanoic acid (G) (1.0 g, 4.6 mmol) was dissolved in dry THF (20 mL) and borane dimethyl sulphide (3 mL, 1.1 equiv.) was slowly added under N2 atmosphere. The mixture was stirred at room temperature for 4 hr. Water was added to the solution was extracted using ethyl acetate. The organic extract was washed with 1N HCl, water and saturated sodium bicarbonate solution successively. After drying (MgSO4), the solvent was evaporated to give a clear oil. The crude oil was purified by column chromatography [eluant: hexane/ethyl acetate (8:2)]. Yield: 0.45 g (48%) was extracted The organic extract was washed with 1N HCl, water and saturated sodium bicarbonate solution successively After drying (MgSO4) the solvent was evaporated to give a clear oil The crude oil was purified by column chromatography [eluant: hexane/ethyl acetate (8:2)]

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Five (5) mg of the oleic acid-stabilized CdSe quantum dots and 50 mg of 1-mercapto-1-undecanol were mixed with 5 ml of chloroform and 5 ml of ethanol. The mixture was then sonicated for 3 hours. Then, 40 ml of chloroform was added to the mixture to obtain a precipitate of 11-mercapto-1-undecanol capped CdSe quantum dots. The precipitate was dissolved in ethanol and dimethyl sulfoxide (“DMSO”). The mixture was then sonicated for 3 hours