* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
A mixture of 3-fluoro-2-pyridinecarboxaldehyde (4 g, 32 mmol) and hydrazine (20.5 g) was kept at 115 0C for 7 hr, then cooled to rt. The reaction mixture was diluted with water and extracted with EtOAc. The organic phases were combined, washed with brine, and dried. Concentration followed by flash chromatography afforded 1 H-pyrazolo[4,3-b]pyridine (2.3 g, 60.4percent).
Reference：
[1] Patent: WO2008/71451, 2008, A1, . Location in patent: Page/Page column 52
[2] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 15, p. 4211 - 4219
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 23, p. 6998 - 7003
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 6, p. 1852 - 1856
[5] Patent: WO2011/100607, 2011, A1, . Location in patent: Page/Page column 78
[6] ACS Chemical Neuroscience, 2016, vol. 7, # 9, p. 1192 - 1200
[7] Patent: WO2017/133657, 2017, A1, . Location in patent: Page/Page column 60; 61
[8] Patent: WO2017/133667, 2017, A1, . Location in patent: Page/Page column 172
2
[ 372-47-4 ]
[ 68-12-2 ]
[ 31224-43-8 ]
Yield
Reaction Conditions
Operation in experiment
60%
Stage #1: With 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium In diethyl ether; hexane at -70 - -60℃; for 1.5 h; Stage #2: at -70℃; for 1 h;
To a solution of DABCO (8.8 g, 78.2 mmol) in anhydrous diethyl ether (250 mL) at -25° C. was added n-BuLi (1.6 M in hexanes, 49 mL, 78.2 mmol). The mixture was stirred between -25 to -10° C. for 45 min and then cooled to -70° C. To the above solution was added 3-fluoropyridine (5.9 mL, 71 mmol) dropwise. The reaction was stirred between -70 to -60° C. for 1.5 h before DMF (11.0 mL, 2.0 eq.) was added. After 1.0 h stirring at -70° C., water (150 mL) was added and warmed up to rt. The layers were separated and the aqueous layer was extracted with methylene chloride (5.x.100 mL). The combined organic layer was washed with brine and dried over Na2SO4. After removal of solvent, the crude was purified by silica gel column chromatography using gradient EtOAc in hexanes to give 5.4 g (55-60percent yield) of 65A. 1H NMR (400 MHz, CDCl3) δ ppm 7.54-7.57 (m, 2H) 8.61 (d, J=2.20 Hz, 1H) 10.20 (s, 1H).
43%
Stage #1: With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at -78 - -20℃; for 2.41667 h; Stage #2: at -78℃; for 2.16667 h;
n-Butyllithium (2.0 M in hexanes, 27.5 ml, 55 mmol) was added dropwise over 10 minutes at -200C to a solution of Λ/,Λ/,Λ/',Λ/'-tetramethylethylenediamine (7.5 ml, 50 mmol) in anhydrous diethyl ether (200 ml). The reaction mixture was stirred at -200C for 1 hour, then it was cooled to -78°C and 3- fluoropyridine (4.3 ml, 50 mmol), in diethyl ether (10 ml), was added dropwise over 15 minutes at - 78°C. The reaction mixture was stirred at" ι-78°C for 1 hour, after which time N1N- Dimethylformamide (4.3 ml, 55 mmol), in diethyl ether (10 ml), was added dropwise over 10 minutes at -78°C. It was stirred for 2 hours, then poured carefully onto a rapidly stirring ice/water mixture (300 ml). The mixture was stirred for 20 minutes, then diluted with ethyl acetate (200 ml). The layers were separated and the aqueous layer was further extracted with dichloromethane (4 x 50 ml). The organic solutions were combined and concentrated under reduced pressure, and the resulting crude product was purified by column chromatography on silica gel using EPO <DP n="49"/>dichloromethane:pentane as eluant (0:100 to 60:40 v/v) to yield the title compound (2.7 g, 43percent) as a solid.1H NMR (400MHz, CDCI3): δ 7.56-7.60 (m, 2H)1 8.63 (m, 1 H), 10.22 (s, 1 H).
Reference：
[1] Patent: US2010/227894, 2010, A1, . Location in patent: Page/Page column 55
[2] Patent: WO2006/114706, 2006, A1, . Location in patent: Page/Page column 47-48
[3] Tetrahedron, 1983, vol. 39, # 12, p. 2009 - 2021
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 23, p. 6998 - 7003
[5] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 6, p. 1852 - 1856
[6] Patent: WO2012/177896, 2012, A1, . Location in patent: Page/Page column 89-90
[7] Organic Process Research and Development, 2007, vol. 11, # 4, p. 716 - 720
Stage #1: With 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium In diethyl ether; hexane at -78 - -20℃; for 2 h; Stage #2: at -60 - -20℃; for 4 h;
ra-Butyl lithium (1.6 M in hexanes, 6.86 mL, 11.0 mmol) was added to a stirred solution of 1,4- diazobicyclo[2.2.2]-octane (1.23 g, 11.0 mmol) in dry Et2O (55 mL) at -780C under N2. The reaction was warmed to -200C and stirred for 1 h. The reaction was cooled to -78 0C and a solution of 3- fluoropyridine (1.07 g, 11.0 mmol) in Et2ψ (5.5 mL) was added dropwise via cannula. The reaction was warmed to -600C and stirred for 1 h after which time a yellow precipitate appeared. DMF (803 mg, 847 μL, 12.1 mmol) was added dropwise and the reaction was gradually warmed to -20 0C over 4 h. Water (20 mL) was added and the mixture was extracted with Et2O (3 x 40 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 25 x 160 mm, 0-60percent EtOAc in hexanes gradient) to afford 3-fluoropyridine-2- carbaldehyde (152.3 mg, 11percent). Ry= 0.23 (20percent EtOAc/hexanes). LCMS calc. = 126.0; found = 125.9 (M+l)+. 1H NMR (500 MHz, CDCl3): δ 10.14 (d, J = 2.4 Hz, 1 H); 8.57 (m, 1 H); 7.57-7.53 (m, 2 H).
With n-butyllithium In diethyl ether; hexane; water; N,N-dimethyl-formamide
2-Formyl-3-fluoropyridine Dry ethyl ether (500 mL), n-BuLi (1.6M in hexane, 62.5 mL, 0.1 mol), and dry 1,4-diazabicyclo[2.2.2]octane (DABCO) (11.56 g, 0.1 mol) were introduced into a 1 L flask under a dry N2 stream at -60° C. and the resulting cloudy solution was stirred for 1 hour at -20° C. The mixture was then cooled to -75° C. and an ethyl ether (50 mL) solution of 3-fluoropyridine (9.81 g, 0.1 mol) was added dropwise and stirring continued for 11/2 hours at -60° C. The mixture was recooled to -75° C., dry N,N-dimethylformamide (8.52 mL, 0.11 mol) dissolved in ethyl ether (50 mL) was added dropwise and the mixture stirred for 2 hours at -75° C. Water (175 mL) was introduced slowly at -10° C., the aqueous layer extracted with ethyl acetate (5*200 mL), and the combined extracts were dried over anhydrous sodium sulfate. Solvent removal produced a dark brown oil which after vacuum distillation and purification by chromatography on silica gel provided 4.4 g (35percent) of the titled product as an off-white crystalline solid: mp 48°-49° C.; IR (CHCl3, cm-1) 3071, 3020, 2873, 2842, 1720, 1588, 1461, 1441; 1 H NMR (300 MHz, CDCl3) δ10.21 (s, 1H), 8.62 (m, 1H), 7.57 (m, 2H); MS (FD) m/e 125 (M+);
Reference：
[1] Patent: US5593993, 1997, A,
7
[ 372-47-4 ]
[ 31224-43-8 ]
Reference：
[1] Patent: US5716971, 1998, A,
8
[ 1319649-53-0 ]
[ 31224-43-8 ]
Reference：
[1] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
9
[ 1824-81-3 ]
[ 31224-43-8 ]
Reference：
[1] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
10
[ 3430-10-2 ]
[ 31224-43-8 ]
Reference：
[1] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
11
[ 22280-60-0 ]
[ 31224-43-8 ]
Reference：
[1] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
12
[ 28489-45-4 ]
[ 31224-43-8 ]
Reference：
[1] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
13
[ 22280-62-2 ]
[ 31224-43-8 ]
Reference：
[1] Journal of Fluorine Chemistry, 2011, vol. 132, # 8, p. 541 - 547
2-Hydroxymethyl-3-fluoropyridine A solution of 2-formyl-3-fluoropyridine (4.0 g, 32 mmol) and sodium borohydride (309 mg, 8 mmol) in absolute ethanol (40 mL) was stirred at 0° C. for 15 minutes and at room temperature for 1 hour. The reaction was quenched with saturated aqueous ammonium chloride (5 mL) and filtered through diatomaceous earth to remove solids. The filtrate was evaporated and the resultant white solid was dissolved in ethyl acetate and water. The aqueous layer was extracted with ethyl acetate (5*30 mL) and the combined extracts were dried over anhydrous sodium sulfate. Solvent removal provided 3.78 g (93percent) of the titled product as a pale yellow oil: IR (CHCl3, cm-1) 3607, 3439, 3019, 1607, 1576, 1451, 1416, 1312, 1257, 1218, 1209, 1167, 1105, 1053, 857, 803; 1 H NMR (300 MHz, CDCl3) δ8.38 (m, 1H), 7.39 (m, 1H), 7.26 (m, 1H), 4.83 (s, 2H), 3.73 (br s, 1H); MS (FD) m/e 127 (M+);
Reference：
[1] Patent: US5593993, 1997, A,
16
[ 31224-43-8 ]
[ 124-41-4 ]
[ 51984-46-4 ]
Yield
Reaction Conditions
Operation in experiment
45%
Stage #1: at 80℃; for 4 h; Stage #2: With sodium tetrahydroborate In methanol at 0℃; for 0.333333 h;
To a flask charged with 3-fluoropicolinaldehyde (400 mg, 3.20 mmol) was added sodium methoxide (15 mL, 7.50 mmol) (0.5M in MeOH ). The mixture was stirred at 80 0C for 4h. The reaction mixture was then cooled to 00C with an ice bath and NaBH4 (90 mg, 2.38 mmol) was added to the mixture was stirred at 00C for 20 min before ice was added to the mixture. After concentration in vacuo, the residue was purified with ISCO MPLC (40- 100percent EtOAc/hexane) to yield the title compound as a white solid (200 mg, 45.0 percent). 1H NMR (DMSO-de) δ 8.11 (dd, 1 H), 7.41 (dd, 1 H), 7.31 (dd, 1 H), 4.83 (t, 1 H), 4.54 (d, 2 H), 3.82 (s, 3 H). MS (M+H+) = 140.
A mixture of 3-fluoro-2-pyridinecarboxaldehyde (4 g, 32 mmol) and hydrazine (20.5 g) was kept at 115 0C for 7 hr, then cooled to rt. The reaction mixture was diluted with water and extracted with EtOAc. The organic phases were combined, washed with brine, and dried. Concentration followed by flash chromatography afforded 1 H-pyrazolo[4,3-b]pyridine (2.3 g, 60.4%).
With hydrazine; at 110℃; for 16h;
3-bromo-lH-pyrazolo[4,3-b]pyridine (2). A mixture of 3-fluoro-2-formylpyridine (1) (1.02 g, 8.15 mmol) and anhydrous hydrazine (2 mL) was heated to 110 C. After 16h, the rxn was poured onto ice water and extracted with EtOAc (3 x 50 mL). The collected organic layers were washed with Brine (100 mL), dried (MgS04), filtered and concentrated to provide a dark brown oil.LCMS: RT = 0.102 min, >98% (at) 254 nM, m/z = 120.2 [M + H]+.The crude residue was dissolved in 2M NaOH (10 mL) and a solution of Br2 (0.2 mL) in 2M NaOH (5 mL) was added dropwise. After 3h at rt, NaHS03 (aqueous) (1 mL) was added followed by 4N HCl (~6 mL). A solid precipitated and was collected by filtration and air dried affording an off-white solid (463 mg, 29% yield over 2 steps).LCMS: RT = 0.270 min, >98% (at) 254 nM, m/z = 200.0 [M + H]+.
With hydrazine hydrate; at 120℃; for 16h;
Intermediate A-11H-Pyrazolo [4, 3-b] pyridine A solution of 3-fluoropicolinaldehyde (12.5 g, 100 mmol) in N2H4. H2O (80, 200 mL) was stirred at 120 for 16 h. After TLC (petroleum etherEtOAc 51) showed the reaction was completed, the mixture solution was poured into water (400 mL) and extracted by EtOAc (400 mL). The organic layer was then washed with brine, dried over anhy. Na2SO4, filtered, and concentrated in vacuo to give a crude title compound (11 g, 96yield) as yellow solid. MS 120.3 [M+H] +. 1H NMR (400 MHz, CHCl3-d1) delta 11.15 (br, 1H) , 8.65-8.63 (m, 1H) , 8.37 (s, 1H) , 7.90 (d, J 11.6 Hz, 1H) , 7.36-7.32 (m, 1H).
With sodium borohydrid; In ethanol; ethyl acetate;
2-Hydroxymethyl-3-fluoropyridine A solution of 2-formyl-3-fluoropyridine (4.0 g, 32 mmol) and sodium borohydride (309 mg, 8 mmol) in absolute ethanol (40 mL) was stirred at 0° C. for 15 minutes and at room temperature for 1 hour. The reaction was quenched with saturated aqueous ammonium chloride (5 mL) and filtered through diatomaceous earth to remove solids. The filtrate was evaporated and the resultant white solid was dissolved in ethyl acetate and water. The aqueous layer was extracted with ethyl acetate (5*30 mL) and the combined extracts were dried over anhydrous sodium sulfate. Solvent removal provided 3.78 g (93percent) of the titled product as a pale yellow oil: IR (CHCl3, cm-1) 3607, 3439, 3019, 1607, 1576, 1451, 1416, 1312, 1257, 1218, 1209, 1167, 1105, 1053, 857, 803; 1 H NMR (300 MHz, CDCl3) delta8.38 (m, 1H), 7.39 (m, 1H), 7.26 (m, 1H), 4.83 (s, 2H), 3.73 (br s, 1H); MS (FD) m/e 127 (M+);
To a flask charged with 3-fluoropicolinaldehyde (400 mg, 3.20 mmol) was added sodium methoxide (15 mL, 7.50 mmol) (0.5M in MeOH ). The mixture was stirred at 80 0C for 4h. The reaction mixture was then cooled to 00C with an ice bath and NaBH4 (90 mg, 2.38 mmol) was added to the mixture was stirred at 00C for 20 min before ice was added to the mixture. After concentration in vacuo, the residue was purified with ISCO MPLC (40- 100percent EtOAc/hexane) to yield the title compound as a white solid (200 mg, 45.0 percent). 1H NMR (DMSO-de) delta 8.11 (dd, 1 H), 7.41 (dd, 1 H), 7.31 (dd, 1 H), 4.83 (t, 1 H), 4.54 (d, 2 H), 3.82 (s, 3 H). MS (M+H+) = 140.
Stage #1: 3-fluoropyridine-2-carbaldehyde; methylamine In methanol at 0℃; for 2h;
Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃;
1.1.15
Example 1.1.15: Synthesis of 1 -(3 -fluoropyridin-2-yl)-N-methylmethanamine[0294] Ti(0'PR)4 (Commercial source: sigma-aldrich) (2.95 g, 10.4 mmol) was added with stirring to MeNH2(Commercial source: sigma-aldrich) (2.0 M in MeOH, 12 ml, 23.7 mmol) under Ar. After 5 min. the aldehyde, 3-fluoropicolinaldehyde (1.0 g, 7.99 mmol)(Commercial source: sigma-aldrich) was added, and the solution was stirred for 2 h. The reaction was cooled to 0° C and the NaBH4 (395 mg, 10.4 mmol) was added. The solution was stirred at 0° C to RT overnight. After quenching the reaction with water the mixture was filtered through celite to remove the white precipitate. Then MeOH was removed in vacuo. The residue was diluted with EtOAc. The resulting solution was washed with water (x3), brine (xl), and dried over Na2S04. The inorganics were filtered off, and the solvent was removed in vacuo to give the crude product. Purification via column chromatography yielded the pure l-(3-fluoropyridin-2-yl)-N-methylmethanamine in 67% yield.
With sodium hydrogensulfite In N,N-dimethyl-formamide at 120℃; for 8h;
1.1 Production Example 1(1)
Production Example 1(1) A mixture of N2-methyl-5-trifluoromethylpyridin-2 , 3- diamine (0.76 g) , 3-fluoropyridin-2-carboaldehyde (0.50 g) , sodium hydrogen sulfite (0.50 g) and DMF (3 ml) was stirred at 120°C for 8 hours. To the cooled reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2- (3- fluoropyridin-2-yl ) -3-methyl-6-trifluoromethyl-3H- imidazo[ 4 , 5-b] pyridine (0.43 g) , which is hereinafter referred to as "intermediate compound (M6-2)". Intermediate compound (M6-2) 1H-NMR (CDC13) δ: 8.75 (lH,d), 8.66-8.63 (lH,m), 8.40 (lH,d), 7.73-7.67 (lH,m), 7.56-7.51 (lH,m), 4.16 (3H,s).
0.43 g
With sodium hydrogensulfite In N,N-dimethyl-formamide at 120℃; for 8h;
1 (1) Production example 1 (1)
Production example 1 (1) A mixture of N2-methyl-5-trifluoromethylpyridine-2,3-diamine 0.76 g, 3-fluoropyridine-2-carboaldehyde 0.50 g, sodium hydrogensulfite 0.50 g, and DMF 3 mL was stirred at 120°C for 8 hr. To the reaction mixture allowed to cool was added saturated aqueous sodium bicarbonate, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resultant residue was treated with silica gel column chromatography to give 2-(3-fluoropyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Intermediate compound (M6-2)) 0.43 g. Intermediate compound (M6-2) (0615) 1H-NMR(CDCl3)δ: 8.75(1H, d), 8.66-8.63(1H, m), 8.40(1H, d), 7.73-7.67(1H, m), 7.56-7.51(1H, m), 4.16(3H, s).
0.43 g
With sodium hydrogensulfite In N,N-dimethyl-formamide at 120℃; for 8h;
1.1 Production example 1 (1)
Production example 1 (1) A mixture of N2-methyl-5-trifluoromethylpyridine-2,3-diamine 0.76 g, 3-fluoropyridine-2-carboaldehyde 0.50 g, sodium hydrogensulfite 0.50 g, and DMF 3 mL was stirred at 120°C for 8 hr. To the reaction mixture allowed to cool was added saturated aqueous sodium bicarbonate, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resultant residue was treated with silica gel column chromatography to give 2-(3-fluoropyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Intermediate compound (M6-2)) 0.43 g. 1H-NMR(CDCl3)δ: 8.75(1H, d), 8.66-8.63(1H, m), 8.40(1H, d), 7.73-7.67(1H, m), 7.56-7.51(1H, m), 4.16(3H, s).
0.43 g
With sodium hydrogensulfite In N,N-dimethyl-formamide at 120℃; for 8h;
1.1 Production Example 1 (1)
A mixture of N2-methyl-5-trifluoromethylpyridine-2,3-diamine 0.76 g, 3-fluoropyridine-2-carboaldehyde 0.50 g, sodium hydrogensulfite 0.50 g, and DMF 3 mL was stirred at 120° C. for 8 hr. To the reaction mixture allowed to cool was added saturated aqueous sodium bicarbonate, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resultant residue was treated with silica gel column chromatography to give 2-(3-fluoropyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Intermediate compound (M6-2)) 0.43 g. Intermediate Compound (M6-2) (1030) (1031) 1H-NMR (CDCl3) δ: 8.75 (1H, d), 8.66-8.63 (1H, m), 8.40 (1H, d), 7.73-7.67 (1H, m), 7.56-7.51 (1H, m), 4.16 (3H, s).
0.43 g
With sodium hydrogensulfite In N,N-dimethyl-formamide at 120℃; for 8h;
P.1.1
A mixture of N2-methyl-5-trifluoromethylpyridine-2,3-diamine 0.76 g, 3-fluoropyridine-2-carboaldehyde 0.50 g, sodium hydrogensulfite 0.50 g, and DMF 3 mL was stirred at 120° C for 8 hr. To the reaction mixture allowed to cool was added saturated aqueous sodium bicarbonate, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resultant residue was treated with silica gel column chromatography to give 2-(3-fluoropyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Intermediate compound (M6-2)) 0.43 g. 1H-NMR(CDCl3)δ: 8.75(1H, d), 8.66-8.63(1H, m), 8.40(1H, d), 7.73-7.67(1H, m), 7.56-7.51(1H, m), 4.16(3H, s).
0.43 g
With sodium hydrogensulfite In N,N-dimethyl-formamide at 120℃; for 8h;
1.1
Production example 1 (1) A mixture of N2-methyl--5-trifluoromethylpyridine-2,3-diamine 0.76 g, 3-fluoropyridine-2-carbaaldehyde 0.50 g, sodium hydrogensulfite 0.50 g, and DMF 3 mL was stirred at 120° C for 8 hr. To the reaction mixture allowed to cool was added saturated aqueous sodium bicarbonate, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resultant residue was treated with silica gel column chromatography to give 2-(3-fluoropyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Intermediate compound (M6-2)) 0.43 g. Intermediate compound (M6-2)1H-NMR(CDCl3)δ: 8.75(1H, d), 8.66-8.63(1H, m), 8.40(1H, d), 7.73-7.67(1H, m), 7.56-7.51(1H, m), 4.16(3H, s).
With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 16h;
a) To a 100-mL round-bottomed flask was added <strong>[40594-29-4]2,4-difluorophenylhydrazine hydrochloride</strong> (1.48 g, 8.2 mmol), 3-fluoro-2-formylpyridine (1.00 g, 8 mmol), K2CO3 (3.32 g, 24 mmol), and DMF (10 mL). The slurry was heated to 120 C. in an oil bath for 16 hours at which point the reaction mixture was cooled and poured into 25 mL of H2O. The brown precipitate was collected via filtration and washed with 3×H2O. The solid was dissolved in CH2Cl2, washed with brine, dried on Na2SO4, filtered, and concentrated to a brown solid. This solid was dissolved in EtOAc, eluted through a silica plug, and concentrated to a brown solid (1.58 g, 85%). MS: (ES) m/z calculated for C12H8F2N3 [M+H]+ 232.1, found 232.1.
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