| 51% |
|
A solution of <strong>[188813-02-7]3-bromo-5-fluorobenzaldehyde</strong> (CXX) (20.0 g, 98.2 mmol, 1.0 eq) in MeOH (1.8 L) was added N?,N?-dimethylethane-1,2-diamine (21.5 mL, 196.4 mmol, 2.0 eq). The pH was adjusted to 6 using HOAc and stirred for 1 h. NaCNBH3 (8.6 g, 137.5 mmol, 1.4 eq) was added and stirred at room temperature overnight. The MeOH was removed under vacuum and the residue was partitioned between CHC13 and saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and evaporated under vacuum. The cmde product was purified on a silica gel column (100% CHC13 -* 3:97 MeOH[7N NH3j:CHC13) to produce N?-(3-bromo-5- fluorophenyl)-N2,N2-dimethylethane-1,2-diamine (CXXI) as a yellow oil (13.0 g, 49.9 mmol, 51% yield). ?H NMR (DMSO-d6, 500 MHz) ppm 1.28 (s, 6H), 2.39 (t, J4Hz, 2H), 3.07 (q, J6Hz, 2H), 6.10 (t, J5Hz, 1H), 6.38 (td, J12Hz, J2Hz, 1H), 6.51 (td, J8.6Hz, J2Hz, 1H), 6.61 (t, J2Hz, 1H); ESIMS found C,0H,4BrFN2 mlz 261.0 (M+H). |
| 51% |
With sodium cyanoborohydride; acetic acid; In methanol; at 20℃;pH 6.0; |
j0711j A solution of <strong>[188813-02-7]3-bromo-5-fluorobenzaldehyde</strong> (CXI) (20.0 g, 98.2 mmol, 1.0 eq) in MeOH (1.8 L) was added N?,N?-dimethylethane-1,2-diamine (21.5 mL, 196.4 mmol, 2.0 eq). The pH was adjusted to 6 using HOAc and stirred for 1 h. NaCNBH3 (8.6 g, 137.5 mmol, 1.4 eq) was added and stirred at room temperature overnight. The MeOH was removed under vacuum and the residue was partitioned between CHC13 and saturated aqueous NaHCO3. The organic layer was dried over Mg504 and evaporated under vacuum. The cmde product was purified on a silica gel column (100% CHC13 -* 3:97 MeOH[7N NH3j:CHC13) to produce N?-(3-bromo-5-fluorophenyl)- N2,N2-dimethylethane- 1 ,2-diamine (CXII) as a yellow oil (13.0 g, 49.9 mmol, 51% yield). ?H NMR (DMSO-d6, 500 MHz) ppm 1.28 (s, 6H), 2.39 (t,J4Hz, 2H), 3.07 (q,J=6Hz, 2H), 6.10 (t,J5Hz, 1H), 6.38 (td, J12Hz, J2Hz, 1H), 6.51 (td, J8.6Hz, J2Hz, 1H), 6.61 (t, J2Hz, 1H); ESIMS found C,0H,4BrFN2 mlz 261.0 (M+H). |
| 51% |
|
A solution of <strong>[188813-02-7]3-bromo-5-fluorobenzaldehyde</strong> (CVII) (20.0 g, 98.2 mmol, 1.0 eq) in MeOH (1.8 L) was added N^N^dimethylethane-l^-diamine (21.5 mL, 196.4 mmol, 2.0 eq). The pH was adjusted to 6 using HOAc and stirred for 1 h. NaCNB (8.6 g, 137.5 mmol, 1.4 eq) was added and stirred at room temperature overnight. The MeOH was removed under vacuum and the residue was partitioned between CHCh and saturated aqueous NaHC03. The organic layer was dried over MgS04 and evaporated under vacuum. The crude product was purified on a silica gel column (100% CHC13? 3:97 MeOH[7N NH3]:CHC13) to produce N434>romo-5-fluorophenyl)- N2,N2-dimethylethane-l,2-diamine (CVIII) as a yellow oil (13.0 g, 49.9 mmol, 51% yield). NMR (DMSO- 6, 500 MHz) delta ppm 1.28 (s, 6H), 2.39 (t, J=4Hz, 2H), 3.07 (q, J=6Hz, 2H), 6.10 (t, J=5Hz, IH), 6.38 (td, J=12Hz, J=2Hz, IH), 6.51 (td, J=8.6Hz, J=2Hz, IH), 6.61 (t, J=2Hz, IH); ESIMS found Ci0Hi4BrFN2 mlz 261.0 (M+H). |
| 51% |
|
[0711] A solution of <strong>[188813-02-7]3-bromo-5-fluorobenzaldehyde</strong> (CVIII) (20.0 g, 98.2 mmol, 1.0 eq) in MeOH (1.8 L) was added N^N^dimethylethane-l^-diamine (21.5 mL, 196.4 mmol, 2.0 eq). The pH was adjusted to 6 using HO Ac and stirred for 1 h. NaCNB (8.6 g, 137.5 mmol, 1.4 eq) was added and stirred at room temperature overnight. The MeOH was removed under vacuum and the residue was partitioned between CHCI3 and saturated aqueous NaHC03. The organic layer was dried over MgS04 and evaporated under vacuum. The crude product was purified on a silica gel column (100% CHCI3? 3:97 MeOH[7N NH3]:CHC13) to produce N^3-bromo-5-fluorophenyl)- N2,N2-dimethylethane-l,2-diamine (CIX) as a yellow oil (13.0 g, 49.9 mmol, 51% yield). 'HNMR (DMSO- tf, 500 MHz) delta ppm 1.28 (s, 6H), 2.39 (t, J=4Hz, 2H), 3.07 (q, J=6Hz, 2H), 6.10 (t, J=5Hz, 1H), 6.38 (td, J=12Hz, J=2Hz, 1H), 6.51 (td, J=8.6Hz, J=2Hz, 1H), 6.61 (t, J=2Hz, 1H); ESIMS found CioHi4BrFN2 mlz 261.0 (M+H). |
| 51% |
|
A solution of <strong>[188813-02-7]3-bromo-5-fluorobenzaldehyde</strong> (CXXI) (20.0 g, 98.2 mmol, 1.0 eq) in MeOH (1.8 L) was added N1,N1-dimethylethane-1,2-diamine (21.5 mL, 196.4 mmol, 2.0 eq). The pH was adjusted to 6 using HOAc and stirred for 1 h. NaCNBH3 (8.6 g, 137.5 mmol, 1.4 eq) was added and stirred at room temperature overnight. The MeOH was removed under vacuum and the residue was partitioned between CHCl3 and saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and evaporated under vacuum. The crude product was purified on a silica gel column (100% CHCl3?3:97 MeOH[7N NH3]:CHCl3) to produce N1-(3-bromo-5-fluorophenyl)-N2,N2-dimethylethane-1,2-diamine (CXXII) as a yellow oil (13.0 g, 49.9 mmol, 51% yield). 1H NMR (DMSO-d6, 500 MHz) delta ppm 1.28 (s, 6H), 2.39 (t, J=4 Hz, 2H), 3.07 (q, J=6 Hz, 2H), 6.10 (t, J=5 Hz, 1H), 6.38 (td, J=12 Hz, J=2 Hz, 1H), 6.51 (td, J=8.6 Hz, J=2 Hz, 1H), 6.61 (t, J=2 Hz, 1H); ESIMS found C10H14BrFN2 m/z 261.0 (M+H). |
| 51% |
|
Step 1 A solution of <strong>[188813-02-7]3-bromo-5-fluorobenzaldehyde</strong> (CIV) (20.0 g, 98.2 mmol, 1.0 eq) in MeOH (1.8 L) was added N1,N1-dimethylethane-1,2-diamine (21.5 mL, 196.4 mmol, 2.0 eq). The pH was adjusted to 6 using HOAc and stirred for 1 h. NaCNBH3 (8.6 g, 137.5 mmol, 1.4 eq) was added and stirred at room temperature overnight. The MeOH was removed under vacuum and the residue was partitioned between CHCl3 and saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and evaporated under vacuum. The crude product was purified on a silica gel column (100% CHCl3?3:97 MeOH[7N NH3]:CHCl3) to produce N1-(3-bromo-5-fluorophenyl)-N2,N2-dimethylethane-1,2-diamine (CV) as a yellow oil (13.0 g, 49.9 mmol, 51% yield). 1H NMR (DMSO-d6, 500 MHz) delta ppm 1.28 (s, 6H), 2.39 (t, J=4 Hz, 2H), 3.07 (q, J=6 Hz, 2H), 6.10 (t, J=5 Hz, 1H), 6.38 (td, J=12 Hz, J=2 Hz, 1H), 6.51 (td, J=8.6 Hz, J=2 Hz, 1H), 6.61 (t, J=2 Hz, 1H); ESIMS found C10H14BrFN2 m/z 261.0 (M+H). |
| 51% |
|
Preparation of intermediate 4-(3-((2-(dimethylamino)ethyl)amino)-5-fluorophenyl)pyridine-2,3-diamine (CII) is depicted below in Scheme 20. Step 1 (0886) A solution of <strong>[188813-02-7]3-bromo-5-fluorobenzaldehyde</strong> (XCVIII) (20.0 g, 98.2 mmol, 1.0 eq) in MeOH (1.8 L) was added N1,N1-dimethylethane-1,2-diamine (21.5 mL, 196.4 mmol, 2.0 eq). The pH was adjusted to 6 using HOAc and stirred for 1 h. NaCNBH3 (8.6 g, 137.5 mmol, 1.4 eq) was added and stirred at room temperature overnight. The MeOH was removed under vacuum and the residue was partitioned between CHCl3 and saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and evaporated under vacuum. The crude product was purified on a silica gel column (100% CHCl3?3:97 MeOH[7N NH3]:CHCl3) to produce N1-(3-bromo-5-fluorophenyl)-N2,N2-dimethylethane-1,2-diamine (XCIX) as a yellow oil (13.0 g, 49.9 mmol, 51% yield). 1H NMR (DMSO-d6, 500 MHz) delta ppm 1.28 (s, 6H), 2.39 (t, J=4 Hz, 2H), 3.07 (q, J=6 Hz, 2H), 6.10 (t, J=5 Hz, 1H), 6.38 (td, J=12 Hz, J=2 Hz, 1H), 6.51 (td, J=8.6 Hz, J=2 Hz, 1H), 6.61 (t, J=2 Hz, 1H); ESIMS found C10H14BrFN2 m/z 261.0 (M+H). |
| 51% |
|
Step 1 (0903) A solution of <strong>[188813-02-7]3-bromo-5-fluorobenzaldehyde</strong> (CXIII) (20.0 g, 98.2 mmol, 1.0 eq) in MeOH (1.8 L) was added N1,N1-dimethylethane-1,2-diamine (21.5 mL, 196.4 mmol, 2.0 eq). The pH was adjusted to 6 using HOAc and stirred for 1 h. NaCNBH3 (8.6 g, 137.5 mmol, 1.4 eq) was added and stirred at room temperature overnight. The MeOH was removed under vacuum and the residue was partitioned between CHCl3 and saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and evaporated under vacuum. The crude product was purified on a silica gel column (100% CHCl3?3:97 MeOH[7N NH3]:CHCl3) to produce N1-(3-bromo-5-fluorophenyl)-N2,N2-dimethylethane-1,2-diamine (CXIV) as a yellow oil (13.0 g, 49.9 mmol, 51% yield). 1H NMR (DMSO-d6, 500 MHz) delta ppm 1.28 (s, 6H), 2.39 (t, J=4 Hz, 2H), 3.07 (q, J=6 Hz, 2H), 6.10 (t, J=5 Hz, 1H), 6.38 (td, J=12 Hz, J=2 Hz, 1H), 6.51 (td, J=8.6 Hz, J=2 Hz, 1H), 6.61 (t, J=2 Hz, 1H); ESIMS found C10H14BrFN2 m/z 261.0 (M+H). |
| 51% |
|
Step 1 (0910) A solution of <strong>[188813-02-7]3-bromo-5-fluorobenzaldehyde</strong> (CXIII) (20.0 g, 98.2 mmol, 1.0 eq) in MeOH (1.8 L) was added N1,N1-dimethylethane-1,2-diamine (21.5 mL, 196.4 mmol, 2.0 eq). The pH was adjusted to 6 using HOAc and stirred for 1 h. NaCNBH3 (8.6 g, 137.5 mmol, 1.4 eq) was added and stirred at room temperature overnight. The MeOH was removed under vacuum and the residue was partitioned between CHCl3 and saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and evaporated under vacuum. The crude product was purified on a silica gel column (100% CHCl3?3:97 MeOH[7N NH3]:CHCl3) to produce N1-(3-bromo-5-fluorophenyl)-N2,N2-dimethylethane-1,2-diamine (CXIV) as a yellow oil (13.0 g, 49.9 mmol, 51% yield). ESIMS found C10H14BrFN2 m/z 261.0 (M+H). |
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