944401-65-4|5-Bromo-6-fluoropyridin-2-amine| Ambeed

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Quality Control of [ 944401-65-4 ] Purity: 98% SDS Specification

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Product Details of [ 944401-65-4 ]

CAS No. :	944401-65-4
Formula :	C₅H₄BrFN₂
M.W :	191.00
SMILES Code :	NC1=NC(F)=C(Br)C=C1
MDL No. :	MFCD11848480
InChI Key :	SJXWFNBZBXZDCL-UHFFFAOYSA-N
Pubchem ID :	53418436

Safety of [ 944401-65-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 944401-65-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	36.3
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	38.91 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.47
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.63
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.99
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.43
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.81
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.67

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.54
Solubility	0.545 mg/ml ; 0.00285 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.06
Solubility	1.66 mg/ml ; 0.00871 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.8
Solubility	0.303 mg/ml ; 0.00158 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.31 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.82

Application In Synthesis of [ 944401-65-4 ]

* 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.

Downstream synthetic route of [ 944401-65-4 ]

[ 944401-65-4 ] Synthesis Path-Downstream 1~35

1
[ 944401-65-4 ]
[ 73183-34-3 ]
[ 944401-67-6 ]

Yield	Reaction Conditions	Operation in experiment
35%	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 115℃; for 4.25h;Heating / reflux;	0271] To a dry 50-mL flask was added 5-bromo-6-fluoro-2-pyridylamine(370 mg, 1.93 mmol), potassium acetate (569 mg, 5.8 mmol), 4,4,5,5-tetramethyl-2- <n="104"/>(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (538 mg, 2.12 mmol) and dioxane (15 mL). Argon was bubbled through the solution for 15 minutes, at which time l,l'-bis(diphenylphosphino)ferrocene palladium(II) chloride dichloromethane adduct (79 mg, 0.09 mmol). The reaction was refluxed in a 115 C oil bath for 4 hours under argon. After removal of the volatiles in vacuo, EtOAc (150 mL) was added and the solution was washed with H2O (3x40 mL), with NaCl(sat.) (300 mL), dried over Na2SO4, filtered and concentrated. Purification by SiO2 chromatography (30% EtOAc/hexanes) yielded boronate ester (161 mg, 35%). LCMS (m/z): 157 (MH+ of boronic acid, deriving from in situ product hydrolysis on LC) 1H NMR (CDCl3): delta 7.86 (t, J= 8.4 Hz5 IH), 6.29 (dd, J = 8.1, 2.7 Hz, IH), 4.70 (bs, IH), 1.32 (s, 12H).
35%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 115℃; for 4.0h;Inert atmosphere;	Synthesis of 6-fluoro-5-(4,4,5,5-tetramethyl(l,3,2-dioxaborolan-2-yl))-2- pyridylamine[00110] To a dry 50-mL flask was added 5-bromo-6-fluoro-2-pyridylamine (370 mg, 1.93 mmol), potassium acetate (569 mg, 5.8 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (538 mg, 2.12 mmol) and dioxane (15 mL). Argon was bubbled through the solution for 15 minutes, at which timel,l'-bis(diphenylphosphino)ferrocene palladium(II) chloride dichloro methane adduct (79 mg, 0.09 mmol). The reaction was refluxed in a 115 C oil bath for 4 hours under argon. After removal of the volatiles in vacuo, EtOAc (150 mL) was added and the solution was washed with H20 (3x40 mL), with NaCl(sat.) (300 mL), dried over Na2S04, filtered and concentrated. Purification by Si02 chromatography (30% EtOAc/hexanes) yielded boronate ester(161 mg, 35%). LCMS (m/z): 157 (MH+ of boronic acid, deriving from in situ product hydrolysis on LC) ¾ NMR (CDC13): delta 7.86 (t, J= 8.4 Hz, 1H), 6.29 (dd, J= 8.1, 2.7 Hz, 1H), 4.70 (bs, 1H), 1.32 (s, 12H).

References: [1]Patent: WO2007/84786,2007,A1 .Location in patent: Page/Page column 101-102.
[2]Patent: WO2012/109423,2012,A1 .Location in patent: Page/Page column 24.

2
[ 1597-32-6 ]
[ 944401-65-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	With N-Bromosuccinimide; In acetonitrile; at 0℃; for 3.0h;Inert atmosphere;	A solution of commercially available 6-fluoro-pyridin-2-ylamine (1.0 g, 8.74 mmol, leq.) in acetonitrile (44 mL), protected from light and under nitrogen atmosphere, was set stirring at 0C before adding a solution of N-bromosuccinimide (0.79 g, 8.74 mmol, leq.) in acetonitrile (19 mL) over 30 min. After complete addition, the resulting solution was stirred for an additional 2h30. The reaction mixture was then concentrated under reduced pressure and the residue was dissolved in EtOAc, successively washed with brine and water. The organic layer was dried over Na2S04, filtered and concentrated in vacuo. The crude material was purified by flash column chromatography using a gradient of 25 % to 50 % EtOAc in heptane to give 5-bromo- 6-fluoro-pyridin-2-ylamine (1.45 g, 91%) as a white solid.H-NMR (400 MHz, CDCI3): d 7.55 (t, J= 8.6 Hz, 1H), 6.22 (dd, J= 8.3 Hz, 1.5 Hz, 1H), 4.70 (bs, 2H).13C-NMR (101 MHz, CDC ): d 158.8 (d, J= 235 Hz), 156.7 (d, J= 16 Hz), 144.9 (d, J= 2.9 Hz), 106.7 (d, J= 5.0 Hz), 89.4 (d, J= 38 Hz).
79%	With N-Bromosuccinimide; In acetonitrile; at 20℃; for 72.0h;Darkness; Cooling with ice;	6-fluoropyridine-2-amine (2.40g) was dissolved in acetonitrile (45mL), the absence of light. Under ice-cooling N- bromosuccinimide (3.81 g) was added, the dark, for 3 days and nights stirred at room temperature. After the reaction mixture was concentrated to dryness and the resulting solid was purified by silica gel column chromatography to give the title compound 3.22g (79%).
72%	With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; In N,N-dimethyl-formamide; at 0 - 33℃; for 6.0h;	Add 2-amino-6-fluoropyridine (17.2g, 150mmol, 1eq.) To the reaction flask, 200ml N, N-dimethylformamide, Cool to 0 C. 1,3-dibromo-5,5-dimethylhydantoin (48.1g, 165mmol, 1.1eq.) Soluble in 150ml N, N-dimethylformamide, Then add dropwise to the above reaction system, Reaction at 33 C for 6 hours. After the reaction was completed, 350 ml of water was added to the reaction liquid, and a large amount of white solid precipitated. After stirring for 20 minutes, it was filtered and the filter cake was washed with water. The filter cake was vacuum dried to obtain 21.1 g of off-white solid 2-amino-5-bromo-6-fluoropyridine in 72% yield.

64.56%	With N-Bromosuccinimide; In acetonitrile; at 25℃; for 6.0h;	Into a lOOO-mL round-bottom flask, was placed 6-fluoropyridin-2-amine (30 g, 267.601 mmol, 1 equiv), CH ,CN (500 mL), NBS (52 g, 292.161 mmol, 1.09 equiv). The resulting solution was stirred for 6 hr at 25 degrees C. The resulting solution was diluted with 1000 mL of water. The resulting solution was extracted with 3x500 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2 x2000 ml of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was re-crystallized from PE:EA in the ratio of 5:1. The solids were collected by filtration. This resulted in 33 g (64.56%) of 5- bromo-6-fluoropyridin-2-amine as a white solid. 1H NMR (300 MHz, Chlorofom /, ppm) d 7.61 (t, / = 8.6 Hz, 1H), 6.28 (dd, / = 8.3, 1.4 Hz, 1H), 4.45 (s, 2H).
40%	With N-Bromosuccinimide; In chloroform; at 20℃; for 16.0h;	To a 250 mL round bottom flask, were added 6-fluoro-2-aminopyridine (3 g, 0.0267 mol) and chloroform (90 mL). To the same flask, N-bromosuccinimide (5 g, 0.028 mol) was added. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with chloroform and washed with water. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to get the title compound [2 g, 40 %]. *H NMR (300 MHz, CDC13): delta 7.62 (t, = 9.0 Hz, 1H), 6.27 (m, 1H), 4.58 (s, 2H); LC-MS: 193.1 [M+2H]+.
22%		[0269] To a solution of 6-fluoro-2-pyridylamine (1.0 g, 8.93 mmol) in chloroform(55 mL) was added N-bromosuccinimide (1.59 g, 8.93 mmol). The solution was stirred in the dark for 15 hours, at which time it was added to CH2Cl2 (200 mL) and IN NaOH (50 mL). Upon mixing, the layers were separated and the organic layer was washed with NaCl(sat.) (50 mL), dried over Na2SO4, filtered and concentrated. The crude material was purified by SiO2 chromatography (25% EtOAc/ hexanes) yielding 5-bromo-6-fluoro-2- pyridylamine (386 mg, 22%). LCMS (m/z): 190.9/192.9 (MH+); 1HNMR (CDCl3): delta 7.59 (t, J= 8.7 Hz, IH), 6.25 (dd, J= 8.1, 1.2 Hz, IH), 4.58 (bs, IH).
22%		Synthesis o -bromo-6-fluoro-2-pyridylamine [00108] To a solution of 6-fluoro-2 -pyridylamine (1.0 g, 8.93 mmol) in chloroform (55 mL) was added N-bromosuccinimide (1.59 g, 8.93 mmol). The solution was stirred in the dark for 15 hours, at which time it was added to CH2CI2 (200 mL) and IN NaOH(50 mL). Upon mixing, the layers were separated and the organic layer was washed with NaCl(Sat.) (50 mL), dried over Na2S04, filtered and concentrated. The crude material was purified by Si02 chromatography (25% EtOAc/ hexanes) yielding 5-bromo-6-fiuoro-2- pyridylamine (386 mg, 22%). LCMS (m/z): 190.9/192.9 (MH ); ¾ NMR (CDC13): delta 7.59 (t, J = 8.7 Hz, 1H), 6.25 (dd, J= 8.1, 1.2 Hz, 1H), 4.58 (bs, 1H).
	With N-Bromosuccinimide; In acetonitrile; for 4.0h;	To a stirred solution of 6-fluoro-pyridin-2-ylamin (1.0 g, 8.93 mmol) in acetonitrile (50 mL), protected from light and under nitrogen atmosphere, N-bromosuccinimide (0.79 g, 4.46 mmol) was added. After 1 hour, an additional portion of N-bromosuccinimide (0.79 g, 4.46 mmol) was added and the stirring was continued for 3 hours. The volatiles were removed under reduced pressure and the crude material was purified by flash column chromatography using a gradient of 25% to 30% ethyl acetate in hexane to give 5-bromo-6-fluoro-pyridin-2-ylamine (1.45 g) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) delta: 7.60 (t, J=8.59 Hz, 1H) 6.15-6.36 (m, 1H) 4.58 (br. s., 2H) ESMS: m/z 193.34 [M+1]+ for 81Br isotope
	With N-Bromosuccinimide; In acetonitrile; at 10 - 20℃; for 1.5h;	NBS (50. Og, 280.99mmol) was added slowly to 6-fluoropyridin-2-amine (30g, 267.61mmol) in MeCN (300mL) cooled to 10-20C over a period of 30 minutes. The resulting solution was stirred at ambient temperature for 60 minutes then the solvent removed under reduced pressure. The residue was diluted with water, the precipitate collected by filtration, washed with water (200mL) and dried under vacuum to afford the desired material (50. Og, 98%) as a white solid, which was used without further purification. NMR Spectrum: 1H MR (300MHz, DMSO-d6) delta 6.29 (1H, d), 6.57 (2H, bs), 7.65 (1H, t). Mass Spectrum: m/z (ES+)[M+H]+ = 191.
	With N-Bromosuccinimide; In acetonitrile; at 10 - 30℃; for 1.5h;Inert atmosphere;	NBS (50. Og, 280.99mmol) was added slowly to 6-fluoropyridin-2-amine (30 g, 267.61 mmol) in MeCN (300 mL) cooled to 10-20C over a period of 30 minutes. The resulting solution was stirred at ambient temperature for 60 minutes then the solvent removed under reduced pressure. The residue was diluted with water, the precipitate collected by filtration, washed with water (200 mL) and dried under vacuum to afford the desired material (50.0 g, 98%) as a white solid, which was used without further purification. NMR Spectrum: JH NMR (300MHz, DMSO-d6) delta 6.29 (1H, d), 6.57 (2H, bs), 7.65 (1H, t). Mass Spectrum: m z (ES+)[M+H]+ = 191.
	With N-Bromosuccinimide;	Example 59 Synthesis of 6-fluoropyridin-2-amine. A mixture of 6-fluoropyridin-2-amine (3 g, 26.8 mmol) and N-bromosuccinimide (5.25 g, 29.5 mmol) in dry CH3CN (20 mL) was stirred at 0 C. for 2 h. Water (100 mL) was added and the mixture was extracted with EtOAc (100 mL*3). The combined organic layers were concentrated and purified by silica gel chromatography (EA/PE=1/5) to give 5-bromo-6-fluoropyridin-2-amine (4.31 g, yield: 84.2%) as a white solid. ESI-MS [M+H]+: 191.0.

References: [1]Patent: WO2019/149965,2019,A1 .Location in patent: Page/Page column 53-55.
[2]Patent: WO2019/214681,2019,A1 .Location in patent: Paragraph 0132-0134; 0143-0145; 0269; 0274-0275; 0294-0296.
[3]Patent: JP5851663,2016,B1 .Location in patent: Paragraph 0179.
[4]Journal of labelled compounds and radiopharmaceuticals,2013,vol. 56,p. 321 - 324.
[5]Patent: CN110845401,2020,A .Location in patent: Paragraph 0021-0024; 0034-0037; 0047-0050.
[6]Patent: WO2020/41406,2020,A1 .Location in patent: Page/Page column 235.
[7]Patent: WO2014/125426,2014,A1 .Location in patent: Page/Page column 74.
[8]Patent: WO2007/84786,2007,A1 .Location in patent: Page/Page column 101.
[9]Patent: WO2012/109423,2012,A1 .Location in patent: Page/Page column 23-24.
[10]Patent: US2008/221149,2008,A1 .Location in patent: Page/Page column 23.
[11]Patent: WO2015/170081,2015,A1 .Location in patent: Page/Page column 103-104.
[12]Patent: WO2017/46216,2017,A1 .Location in patent: Page/Page column 77.
[13]Patent: US2019/284182,2019,A1 .

3
[ 551001-79-7 ]
[ 944401-65-4 ]
[ 1054629-56-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; In ethanol; at 140℃; for 0.25h;Microwave;	5-Methoxybenzofuran boronic acid (230 mg, 1.20 mmol), <strong>[944401-65-4]5-bromo-6-fluoro-pyridin-2-ylamine</strong> (191 mg, 1.00 mmol), Pd(PPh3)2Cl2 (16.8 mg, 0.024 mmol) and Et3N (317 muL, 2.27 mmol) were mixed in EtOH (10 mL) in a microwave vial. The reaction mixture was stirred at 140 C. for 15 minutes in a microwave reactor. The volatiles were then removed under reduced pressure, the residue was suspended in water and the product was extracted with ethyl acetate. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Purification of the crude product by flash column chromatography using 25% ethyl acetate in hexane gave 6-fluoro-5-(5-methoxy-benzofuran-2-yl)-pyridin-2-ylamine (130 mg) as an off-white solid. 1H NMR (400 MHz, CHLOROFORM-d) delta: 8.05-8.21 (m, 1H) 7.36 (d, J=8.59 Hz, 1H) 7.03 (d, J=1.95 Hz, 1H) 6.97 (d, J=3.12 Hz, 1H) 6.86 (dd, J=8.78, 2.54 Hz, 1H) 6.45 (d, J=6.63 Hz, 1H) 4.66 (br. s., 2H) 3.86 (s, 3H)

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4332 - 4337.
[2]Patent: US2008/221149,2008,A1 .Location in patent: Page/Page column 23.
[3]Patent: WO2018/222549,2018,A1 .Location in patent: Paragraph 0129.

Yield	Reaction Conditions	Operation in experiment
60%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 5 - 20℃;	General procedure: 19.1 5-Bromo-6-chloro-pyridin-2-ylamine 6-chloro-pyridin-2-ylamine (purchased from Aldrich) (1.50 g, 11.7 mmol) is dissolved in 15 ml N,N-Dimethylformamide and cooled to 5 C. 1-bromo-pyrrolidine-2,5-dione (2.28 g, 12.8 mmol) is added and the mixture is slowly warmed to room temperature. The mixture is poured onto ice water and the precipitate is collected by filtration and dried under vacuum. Yield: 91% of theory Mass spectrometry (ESI-): m/z=207, 209 [M+H]+

5
[ 2942-13-4 ]
[ 944401-65-4 ]
C₁₃H₁₀FN₃OS [ No CAS ]