[ CAS No. 887266-99-1 ] {[proInfo.proName]}

Name: 887266-99-1|3-Fluoro-4-iodobenzonitrile|98%
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SKU: A115733
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Quality Control of [ 887266-99-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 887266-99-1 ]

SDS Specification

Alternatived Products of [ 887266-99-1 ]

Product Details of [ 887266-99-1 ]

CAS No. :	887266-99-1	MDL No. :	MFCD07782076
Formula :	C₇H₃FIN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NPKQMCCUPXZXFI-UHFFFAOYSA-N
M.W :	247.01	Pubchem ID :	24721521
Synonyms :

Calculated chemistry of [ 887266-99-1 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	43.83
TPSA :	23.79 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.11 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.9
Log Po/w (XLOGP3) :	2.39
Log Po/w (WLOGP) :	2.72
Log Po/w (MLOGP) :	2.79
Log Po/w (SILICOS-IT) :	3.19
Consensus Log Po/w :	2.6

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.32
Solubility :	0.118 mg/ml ; 0.000477 mol/l
Class :	Soluble
Log S (Ali) :	-2.53
Solubility :	0.727 mg/ml ; 0.00295 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.72
Solubility :	0.0473 mg/ml ; 0.000191 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.16

Safety of [ 887266-99-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 887266-99-1 ]

* 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.

Upstream synthesis route of [ 887266-99-1 ]
Downstream synthetic route of [ 887266-99-1 ]

[ 887266-99-1 ] Synthesis Path-Upstream 1~2

1
[ 63069-50-1 ]
[ 887266-99-1 ]

Yield	Reaction Conditions	Operation in experiment
4.0 g	Stage #1: With toluene-4-sulfonic acid In acetonitrile at 22 - 26℃; for 4 h; Stage #2: With potassium iodide; sodium nitrite In water; acetonitrile at 0℃; for 1 h;	A mixture of 4-amino-3-fluorobenzonitrile (5.0 g, 36.76 mmol) and p-toluenesulfonic acid (20.0 g, 105.2 mmol) in acetonitrile (50 mL) was stirred at RT for 4 h. Then aq. solution of NaNO2 (3.8 g, 55.07 mmol) and KI (9.15 g, 55.07 mmol) were added at 0°C and stirred further for lh. After the reaction completion, the reaction mixture was quenched with water, washed with an aqueous solution of NaHSO3 and extracted with EtOAc. The organic layerwas washed with water, brine, dried over Na2SO4 and concentrated to afford 4.0 g of the title product. ‘H NMR (300 MHz, CDC13): 7.94-7.89 (t, J = 8.4 Hz, 1H), 7.34-7.32 (d, J = 7.5 Hz, 1H), 7.21-7.19 (d, J= 8.1 Hz, 1H).

Reference： [1] Patent: WO2016/55947, 2016, A1, . Location in patent: Page/Page column 57
[2] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 23-24, p. 3766 - 3773

2
[ 218632-01-0 ]
[ 887266-99-1 ]

Reference： [1] Patent: WO2016/55947, 2016, A1,

[ 887266-99-1 ] Synthesis Path-Downstream 1~35

1
[ 887266-99-1 ]
[ 1353683-80-3 ]

Yield	Reaction Conditions	Operation in experiment
82%		General procedure: To a solution of ReIO2(PPh3)2 (10 mol %) in toluene (3 mL) were added the nitrile (1 mmol) and PhSiH3 (300 mol %). The reaction mixture was stirred at reflux temperature under air atmosphere and the progress of the reaction was monitored by TLC or 1H NMR. Upon completion, the reaction mixture was cooled to ambient temperature, stirred with charcoal during 3 min and then filtered through a plug of alumina/Celite. To the filtrate was added an ethereal solution of HCl (1.5 mol) to induce the precipitation of amine hydrochloride salts. The solids were isolated upon filtration and then washed with n-hexane to afford the pure amine hydrochloride salts, which are all known compounds.

Reference： [1]Tetrahedron,2011,vol. 67,p. 8183 - 8186

2
[ 887266-99-1 ]
3-fluoro-4-mercaptobenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%		General procedure: Into an oven-dried flask equipped with a magnetic stir bar was added aryl fluoride (1.00 g, 1.0 eq.), Na2S (1.1 eq.) and DMF (5 mL) under argon. The reaction mixture was stirred at room temperature for 1 h. Then 1 M NaOH (50 mL) was added and was washed with CH2Cl2 (2 x 25 mL). The aqueous layer was acidified to pH ~ 1-2 with 6 N HCl and extracted with CH2Cl2 (2 x 50 mL). The combined organic layer was washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to provide a crude residue. To the residue was added 10% HCl (40 mL) and cooled with an ice-water bath. Then zinc dust (4 g) was added and the mixture was stirred for 1 h. Then EtOAc (100 mL) was added and the mixture was stirred for an additional 30 minutes. The organic layer was separated and washed with water (40 mL) and brine (40 mL), dried over MgSO4, filtered and concentrated to provide the desired product with satisfactory purity.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 2548 - 2551

3
[ 887266-99-1 ]
[ 30418-59-8 ]
[ 1386459-71-7 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrabutyl-ammonium chloride; potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 90℃; for 20h;Inert atmosphere;	3-Aminophenylboronic acid (200 mg, 1.29 mmol), <strong>[887266-99-1]3-fluoro-4-iodobenzonitrile</strong> (319 mg, 1.29 mmol), TBACI (35.9 mg, 0.129 mmol) and Pd(PPh3)4 (74.6 mg, 0.064 mmol) were suspended in a mixture of toluene (4mL) and K2C03 1 M in water (4mL). The biphasic mixture was vigorously stirred under argon at 90C for 20 h. The organic layer was separated and the aqueous phase was extracted with toluene (x2). The organic layers were combined, washed with water, dried over Na2S04, filtered and concentrated. The crude residue was purified by column chromatography (c-hexane/EtOAc 3: 1) to give the desired material. MS (LC/MS) [M+H]+ = 213; tR (HPLC, Waters Atlantis, 2.1x30mm, flow 0.6mL/min, CH3CN/H20 5 to 95% in 2.5 min, 95% CH3CN 2 min, 95 to 5% CH3CN, H20 and CH3CN both containing 0.1 % HCOOH): 2.84 min.

Reference： [1]Patent: WO2012/93101,2012,A1 .Location in patent: Page/Page column 237

4
[ 5419-55-6 ]
[ 887266-99-1 ]
[ 1068-55-9 ]
[ 1150114-77-4 ]

Yield	Reaction Conditions	Operation in experiment
55%	With hydrogenchloride; In tetrahydrofuran; diethyl ether; water; ethyl acetate;	Step 1: (4-Cyano-2-fluorophenyl)boronic acid 24.3 ml (48.6 mmol) of a 2 M solution of isopropylmagnesium chloride in diethyl ether were added dropwise to a solution of 10.0 g (40.5 mmol) of <strong>[887266-99-1]3-fluoro-4-iodobenzonitrile</strong> in a mixture of 120 ml of anhydrous THF and 120 ml of anhydrous diethyl ether at -78 C. When the addition had ended, the mixture was stirred further at -78 C. for another 75 min. 15 ml (64.8 mmol) of triisopropyl borate were then added dropwise. The mixture was then stirred at -78 C. for a further 15 min, before the cold bath was removed and the reaction mixture was allowed to warm to RT. After 3 h at RT, 80 ml of 2 M hydrochloric acid were added and the mixture was stirred intensively at RT for 20 min. Thereafter, it was diluted with approx. 400 ml of water. The phases were separated and the aqueous phase was extracted three times with approx. 150 ml of ethyl acetate each time. The combined organic extracts were washed successively with water and saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the mixture was filtered and the filtrated was concentrated to dryness on a rotary evaporator. 3.68 g (55% of th.) of the title compound were obtained, this being employed for subsequent reactions without further purification. LC/MS (method F, ESIneg): Rt=0.53 min, m/z=164 [M-H]-.

Reference： [1]Patent: US2013/196964,2013,A1 .Location in patent: Paragraph 1211; 1212; 1213

5
[ 887266-99-1 ]
[ 1227159-91-2 ]

Reference： [1]Patent: US2013/196964,2013,A1

6
[ 887266-99-1 ]
[ 1227159-92-3 ]

Reference： [1]Patent: US2013/196964,2013,A1

7
[ 887266-99-1 ]
[ 1451993-25-1 ]

Reference： [1]Patent: WO2013/126856,2013,A1

8
[ 887266-99-1 ]
[ 1451998-61-0 ]

Reference： [1]Patent: WO2013/126856,2013,A1

9
[ 142-08-5 ]
[ 887266-99-1 ]
[ 1451998-60-9 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; 8-quinolinol; caesium carbonate; In dimethyl sulfoxide; at 120℃; for 3h;Microwave irradiation; Sealed tube; Inert atmosphere;	[001143] To a microwave vial equipped with a magnetic stir bar were charged 3-fluoro-4- iodobenzonitrile (250 mg, 1.0 mmol), pyridin-2(lH)-one (192 mg, 2.0 mmol), copper (I) iodide (57 mg, 0.30 mmol), quinolin-8-ol (44 mg, 0.30 mmol), and cesium carbonate (650 mg, 2.0 mmol). The vial was sealed, evacuated and backfilled with argon three times, and then dimethyl sulfoxide (2.5 mL) was introduced via syringe. The resulting suspension was purged and backfilled with argon an additional three times, and heated to 120 C for three hours. After cooling to ambient temperature, the mixture was poured into water and extracted with ethyl acetate. The organic layers were collected, dried, evaporated and purified by silica gel chromatography (0-50% EtOAc in hexanes) to afford 3-fluoro-4-(2-oxopyridin-l(2H)- yl)benzonitrile.

Reference： [1]Patent: WO2013/126856,2013,A1 .Location in patent: Paragraph 001142; 001143

10
[ 887266-99-1 ]
[ 1261744-58-4 ]

Yield	Reaction Conditions	Operation in experiment
2 g	With dihydrogen peroxide; potassium carbonate; In dimethyl sulfoxide; at 0 - 20℃; for 2h;	To a solution of <strong>[887266-99-1]3-fluoro-4-iodobenzonitrile</strong> (2.7 g, 0.010 mmol) in DMSO (6.0 mL), K2C03 (0.450 g, 0.003 mmol) and 30% H2O2 (2.4 mL) were added at 0-10C and the reaction mass was stirred at RT for 2 h. After completion of the reaction, the reaction mass was quenched in ice cold water. The obtained solid product was filtered off to afford 2.0 g of the desired title product. 1H NMR (400 MHz, DMSO d6): delta 7.48- 7.51 (m, 2H), 7.66 (br s, 1H), 7.69- 7.70 (m, 1H), 8.09 (brs, 1H).

Reference： [1]Patent: WO2013/186692,2013,A1 .Location in patent: Page/Page column 152

11
[ 887266-99-1 ]
[ 89490-05-1 ]
4-cyclohexen-1-yl-3-fluorobenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
980 mg	With bis-triphenylphosphine-palladium(II) chloride; sodium ethanolate; In ethanol; at 90℃; for 0.25h;Microwave irradiation;	(1) Synthesis of 4-cyclohexen-1-yl-3-fluorobenzonitrile To a mixture of <strong>[887266-99-1]3-fluoro-4-iodobenzonitrile</strong> (1.53 g), 1-cyclohexen-1-yl-boronic acid (938 mg), bis(triphenylphosphine)palladium(II) dichloride (435 mg) and ethanol (9.75 mL), sodium ethoxide (about 20%, solution in ethanol, 5.75 mL) was added and the mixture was stirred at 90C for 15 minutes under irradiation with microwaves. After being cooled to room temperature, the reaction mixture was poured into water and three extractions were conducted with chloroform. The combined organic layers were washed with saturated brine and passed through a phase separator to be concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 100:0-75:25) to give the titled compound as a pale yellow oil (980 mg). 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.63 - 1.84 (m, 4 H) 2.18 - 2.29 (m, 2 H) 2.30 - 2.41 (m, 2 H) 6.01 - 6.10 (m, 1 H) 7.27 - 7.42 (m, 3 H). MS ESI/APCI Dual posi: 224[M+Na]+. MS ESI/APCI Dual nega: 236[M+Cl]-.

Reference： [1]Patent: EP2881384,2015,A1 .Location in patent: Paragraph 0539; 0540

12
[ 887266-99-1 ]
C₇H₄FIN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With trimethylsilylazide; tetrabutyl ammonium fluoride; In neat (no solvent); at 85℃;Inert atmosphere; Sealed tube; Green chemistry;	General procedure: The tetrazole compounds were prepared by a modified literature reported protocol.3 Thus, the aromatic nitrile (1.0 equiv), TBAF.3H2O (0.5 equiv) and TMS-N3 (1.5 equiv) were taken in a screw capped vial equipped with a magnetic stirrer and the resulting mixture was stirred vigorously at 85 oC. The reaction mixture was then transferred to a seperatory funnel and TBAF was removed by washing the organic phase with 1M aqueous HCl solution (20 ml). The organic phase was separated, washed with brine (20 ml) and dried over Na2SO4 and then concentrated in a rotary evaporator. The products were then purified by silica-gel (60-120 mesh) column chromatography or for some cases by recystallisation. Compound 2L was used as a crude mixture for further reaction. The compounds were then characterized by IR, NMR spectroscopy and mass spectrometry. Compounds 2A-B and 2H are reported compounds3 whereas 2C- 2G and 2I- 2L are new.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 2044 - 2050

13
[ 887266-99-1 ]
C₂₈H₂₄FIN₄O₅ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 2044 - 2050

14
[ 887266-99-1 ]
C₁₂H₁₂FIN₄O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 2044 - 2050

Yield	Reaction Conditions	Operation in experiment
4 g		General procedure: Step-1 :- Preparation of 3-chloro-4-iodobenzonitrile A mixture of 4-amino-3-chlorobenzonitrile (3.0 g, 19.66 mmol), /?-toluenesulfonic acid (11.20 g, 55.98 mmol) in acetonitrile (30 mL) was stirred at RT for 4 h. To this mixture, aq. solution of NaN02 (2.03 g, 29.49 mmol in 7 mL water) and KI (4.89 g, 29.49 mmol) was added at 0C and stirred further for 1 h. After the reaction completion, the reaction mixture was quenched with water, washed with an aqueous solution of NaHS03 and extracted with EtOAc. The organic layer was washed with water, brine, dried over Na2S04 and concentrated to afford 4.0 g of the title product. 1H NMR (300 MHz, CDClj ): delta 8.02-7.99 (d, = 8.4 Hz, 1H), 7.71 (s, 1H), 7.23-7.21 (d, = 8.1 Hz, 1H).

16
[ 63069-50-1 ]
[ 887266-99-1 ]

Yield	Reaction Conditions	Operation in experiment
4.0 g		A mixture of <strong>[63069-50-1]4-amino-3-fluorobenzonitrile</strong> (5.0 g, 36.76 mmol) and p-toluenesulfonic acid (20.0 g, 105.2 mmol) in acetonitrile (50 mL) was stirred at RT for 4 h. Then aq. solution of NaNO2 (3.8 g, 55.07 mmol) and KI (9.15 g, 55.07 mmol) were added at 0C and stirred further for lh. After the reaction completion, the reaction mixture was quenched with water, washed with an aqueous solution of NaHSO3 and extracted with EtOAc. The organic layerwas washed with water, brine, dried over Na2SO4 and concentrated to afford 4.0 g of the title product. ?H NMR (300 MHz, CDC13): 7.94-7.89 (t, J = 8.4 Hz, 1H), 7.34-7.32 (d, J = 7.5 Hz, 1H), 7.21-7.19 (d, J= 8.1 Hz, 1H).

Reference： [1]Patent: WO2016/55947,2016,A1 .Location in patent: Page/Page column 57
[2]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3766 - 3773

17
[ 887266-99-1 ]
3-fluoro-4-((4-hydroxyphenyl)ethynyl)benzoic acid [ No CAS ]

Reference： [1]Patent: WO2016/55947,2016,A1

18
[ 887266-99-1 ]
2-phenylbenzo[b]oxepine-8-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2016/55947,2016,A1

19
[ 887266-99-1 ]
3-fluoro-4-((4-hydroxyphenyl)ethynyl)benzonitrile [ No CAS ]

Reference： [1]Patent: WO2016/55947,2016,A1

20
[ 887266-99-1 ]
[ 1066-54-2 ]
3-fluoro-4-((trimethylsilyl)ethynyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In dimethyl sulfoxide; at 22 - 26℃; for 16h;	A mixture of <strong>[887266-99-1]3-fluoro-4-iodobenzonitrile</strong> (1.0 g, 4.06 mmol), trimethylsilyl acetylene (0.595 g,6.07 mmol), CuT (50 mg, 0.26 mmol), PdC12(PPh3)2 (50 mg, 0.07 1 mmol) and TEA (3 mL) in DMSO (7 mL) was stirred at RT for 16 h. After the reaction, the reaction mixture was quenched with water, extracted with EtOAc. The organic layer was washed with water, brine, dried over Na2SO4 and concentrated to afford 750 mg of crude 2-chloro-5-((trimethylsilyl)-ethynyl) benzoate. To this crude solution of 2-chloro-5-((trimethylsilyl)ethynyl)benzoate (500 mg, 1.87 mmol) in DCM (10 mL) was added TBAF (1.0 g, 3.83 mmol) and stirred further at RT for h. Then the reaction mixture was quenched with water, extracted with DCM, washed with water, brine, dried over Na2SO4 and concentrated to afford 450 mg of the title product. ?H NMR (300 MHz, CDC13): 7.61-7.56 (t, J= 7.2 Hz, 1H), 7.44-7.38 (d, J= 8.1 Hz,2H), 3.52(s, 1H).

Reference： [1]Patent: WO2016/55947,2016,A1 .Location in patent: Page/Page column 57

21
[ 218632-01-0 ]
[ 887266-99-1 ]

Reference： [1]Patent: WO2016/55947,2016,A1

22
[ 887266-99-1 ]
(+/-)-(S)-O-3-phenyl-1-(tri-n-butylstannyl)propyl pyrrolidine-1-carbothioate [ No CAS ]
O-(1-(4-cyano-2-fluorophenyl)-3-phenylpropyl) pyrrolidine-1-carbothioate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 1241 - 1251

23
[ 887266-99-1 ]
[ 5467-74-3 ]
4'-bromo-2-fluoro-[1,1'-biphenyl]-4-carbonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3766 - 3773

24
[ 887266-99-1 ]
5-(2-fluoro-4'-(1H-imidazol-1-yl)-[1,1'-biphenyl]-4-yl)-1H-tetrazole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3766 - 3773

25
[ 887266-99-1 ]
2-fluoro-4'-(1H-imidazol-1-yl)-[1,1'-biphenyl]-4-carboxylic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3766 - 3773

26
[ 887266-99-1 ]
2-fluoro-4'-(1H-imidazol-1-yl)-[1,1'-biphenyl]-4-carbonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3766 - 3773

27
[ 110-00-9 ]
[ 887266-99-1 ]
3-fluoro-4-(furan-2-yl)benzonitrile [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4312 - 4318

28
[ 887266-99-1 ]
4-([2,2'-bifuran]-5-yl)-3-fluorobenzonitrile [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4312 - 4318

29
[ 887266-99-1 ]
C₁₁H₅FINO [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4312 - 4318

30
[ 887266-99-1 ]
(3-fluoro-4-(4-methylthiazol-2-yl)phenyl)methanamine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 10875 - 10894

31
[ 887266-99-1 ]
3-fluoro-4-(4-methylthiazol-2-yl)benzonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 10875 - 10894

32
[ 887266-99-1 ]
N-(3-fluoro-4-(4-methylthiazol-2-yl)benzyl)-1-methyl-1H-pyrazole-5-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 10875 - 10894

33
[ 5419-55-6 ]
[ 887266-99-1 ]
[ 1150114-77-4 ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 10875 - 10894

34
[ 887266-99-1 ]
tert-butyl (S)-7,10-dioxo-6-(4-(trifluoromethyl)benzyl)-2,6,9-triazaspiro[4.5]decane-2-carboxylate [ No CAS ]
tert-butyl (S)-9-(4-cyano-2-fluorophenyl)-7,10-dioxo-6-(4-(trifluoromethyl)benzyl)-2,6,9-triazaspiro[4.5]decane-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine; In 1,4-dioxane; at 115℃; for 18h;Inert atmosphere; Sealed tube;	To a mixture of tert- butyl (S)-7,l0-dioxo-6-(4-(trifluoromethyl)benzyl)-2,6,9- triazaspiro[4.5]decane-2-carboxylate (280 mg, 0.63 mmol), Cul (60 mg, 0.32 mmol, 0.5 equiv.), K2CO3 (349 mg, 2.53 mmol, 4.0 equiv.) and aryl iodide (234 mg, 0.95 mmol, 1.5 equiv.) in l,4-dioxane (6 mL) was added N,N-dimethylethylenediamine (0.034 mL, 0.32 mmol, 0.5 equiv.). The resulting mixture was heated at 115 C under N2 for 18 h in a sealed tube, cooled to r.t, filtered through celite, washed with additional dioxane (15 mL) and DCM (30 mL), concentrated under reduced pressure, and purified by silica gel chromatography using EA / Hex (1/1) as eluents to provide 187 mg (54%) of tert-butyl (S)-9-(4-cyano-2- fluorophenyl)-7,l0-dioxo-6-(4-(trifluoromethyl)benzyl)-2,6,9-triazaspiro[4.5]decane-2- carboxylate. LRMS (APCI) m/z 491.1 (M+H) (-C4H9). NMR (400 MHz, Methanol-i/4) d 7.82 - 7.64 (m, 5H), 7.50 (d, J = 8.0 Hz, 2H), 5.15 - 5.02 (m, 1H), 4.81 - 4.57 (m, 3H), 4.00 (d, J = 12.1 Hz, 1H), 3.66 (d, J = 12.3 Hz, 1H), 3.62 - 3.47 (m, 2H), 2.59 - 2.48 (m, 2H),

Reference： [1]Patent: WO2020/47447,2020,A1 .Location in patent: Paragraph 0407

35
[ 887266-99-1 ]
(S)-2-acetyl-5-(1-(4-(trifluoromethyl)phenyl)ethyl)-2,5,8-triazaspiro[3.5]nonane-6,9-dione [ No CAS ]
(S)-4-(2-acetyl-6,9-dioxo-5-(1-(4-(trifluoromethyl)phenyl)ethyl)-2,5,8-triazaspiro[3.5]nonan-8-yl)-3-fluorobenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine; In 1,4-dioxane; at 115℃; for 18h;Inert atmosphere; Sealed tube;	To a mixture of (S)-2-acetyl-5-(l-(4-(trifluoromethyl)phenyl)ethyl)-2,5,8- triazaspiro[3.5]nonane-6,9-dione (102 mg, 0.28 mmol), Cul (26 mg, 0.14 mmol, 0.5 equiv.), K2CO3 (115 mg, 0.83 mmol, 3.0 equiv.) and <strong>[887266-99-1]3-fluoro-4-iodobenzonitrile</strong> (136 mg, 0.55 mmol, 2.0 equiv.) in a tube were added l,4-dioxane (1.5 mL) and N,N- dimethylethylenediamine (15 pL, 0.14 mmol, 0.5 equiv.). The mixture was purged with N2, sealed, heated at 115 C for 18 h, cooled to r.t., and filtered through celite. The solid was washed with l,4-dioxane (20 mL). The filtrate was evaporated in vacuo and purified with reverse phase HPLC using ACN/ water (both with 0.1% formic acid with a gradient from 10 to 100%; Phenomenex Gemini 5 micron C18 column). The collected fractions provided a mixture which was purified again by silica gel chromatography using EA / Hex (3/7) and MeOH/DCM (1/9) as eluents to provide 24 mg (18%) of (S)-4-(2-acetyl-6,9-dioxo-5-(l-(4- (trifluoromethyl) phenyl)ethyl)-2,5,8-triazaspiro[3.5]nonan-8-yl)-3-fluorobenzonitrile. LRMS (APCI) m/z 489.2 (M+H). 1H NMR (400 MHz, Methanol-74) d 7.83 - 7.61 (m, 7H), 5.4 - 5.6 (bs, 1H), 4.82 - 4.43 (m, 5H), 4.37 (d, J = 11.0 Hz, 1H), 2.03 (t, 7 = 6.8 Hz, 3H), 1.88 (d, 7 = 23.1 Hz, 3H).

Reference： [1]Patent: WO2020/47447,2020,A1 .Location in patent: Paragraph 0499

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