[ CAS No. 52215-41-5 ] {[proInfo.proName]}

Name: 52215-41-5|3-Fluoro-5-methylaniline|97%
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Quality Control of [ 52215-41-5 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 52215-41-5 ]

CAS No. :	52215-41-5	MDL No. :	MFCD00077538
Formula :	C₇H₈FN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DPHBKGYVIHTBDG-UHFFFAOYSA-N
M.W :	125.14	Pubchem ID :	2778458
Synonyms :

Calculated chemistry of [ 52215-41-5 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	35.77
TPSA :	26.02 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) :	-5.85 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.6
Log Po/w (XLOGP3) :	1.71
Log Po/w (WLOGP) :	2.14
Log Po/w (MLOGP) :	2.24
Log Po/w (SILICOS-IT) :	2.01
Consensus Log Po/w :	1.94

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.19
Solubility :	0.814 mg/ml ; 0.00651 mol/l
Class :	Soluble
Log S (Ali) :	-1.87
Solubility :	1.68 mg/ml ; 0.0134 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.66
Solubility :	0.273 mg/ml ; 0.00218 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 52215-41-5 ]

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

Application In Synthesis of [ 52215-41-5 ]

* 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 [ 52215-41-5 ]
Downstream synthetic route of [ 52215-41-5 ]

[ 52215-41-5 ] Synthesis Path-Upstream 1~4

1
[ 499-08-1 ]
[ 52215-41-5 ]

Reference： [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2843 - 2852
[2] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1980, p. 829 - 831

2
[ 618-61-1 ]
[ 52215-41-5 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1980, p. 829 - 831
[2] Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2843 - 2852

3
[ 202865-83-6 ]
[ 52215-41-5 ]

Reference： [1] Nature Chemistry, 2017, vol. 9, # 7, p. 681 - 688

4
[ 618-85-9 ]
[ 52215-41-5 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1980, p. 829 - 831

[ 52215-41-5 ] Synthesis Path-Downstream 1~88

1
[ 499-08-1 ]
[ 52215-41-5 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2843 - 2852
[2]Journal of the Chemical Society. Perkin transactions II,1980,p. 829 - 831

2
[ 52215-41-5 ]
[ 93857-90-0 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2843 - 2852

3
[ 618-85-9 ]
[ 52215-41-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1980,p. 829 - 831

4
[ 618-61-1 ]
[ 52215-41-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1980,p. 829 - 831
[2]Journal of Medicinal Chemistry,1991,vol. 34,p. 2843 - 2852

5
[ 52215-41-5 ]
[ 135340-38-4 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2843 - 2852

6
[ 52215-41-5 ]
[ 135340-50-0 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2843 - 2852

7
[ 52215-41-5 ]
[ 135340-66-8 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2843 - 2852

8
[ 52215-41-5 ]
5-Amino-3-[3-chloro-4-(4-chloro-benzoyl)-5-fluoro-benzyl]-3H-[1,2,3]triazole-4-carboxylic acid amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2843 - 2852

9
[ 605661-25-4 ]
[ 52215-41-5 ]
N-[4-(4-amino-6-ethylthieno[2,3-d]pyrimidin-5-yl)phenyl]-N'-(3-fluoro-5-methylphenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		[0628] Amine: <strong>[52215-41-5]3-fluoro-5-methylaniline</strong>. MS (ESI(+)) m/e 422 (M+H)+; 1H NMR (500 MHz, DMSO-d6) delta 1.16 (t, J=7.49 Hz, 3H); 2.30 (s, 3H); 2.65 (q, J=7.49 Hz, 2H); 7.05 (dd, J=8.27, 2.03 Hz, 1H); 7.17 (t, J=8.73 Hz, 1H); 7.31 (d, J=8.73 Hz, 2H); 7.44 (dd, J=12.48, 2.18 Hz, 1H); 7.62 (d, J=8.74 Hz, 2H); 8.27 (s, 1H); 8.89 (s, 1H); 8.95 (s, 1H).

Reference： [1]Patent: US2003/225273,2003,A1 .Location in patent: Page 56

10
[ 50-00-0 ]
[ 52215-41-5 ]
[ 107603-52-1 ]

Yield	Reaction Conditions	Operation in experiment
58%		To a clear solution of 5-fluoro, 3-aminotoluidine (4.00 g, 32.0 mmol) in glacial acetic acid (193 mL) was added paraformaldehyde (9.40 g, 313 mmol) followed by sodium cyanoborohydride (9.48 g, 151 mmol). Bubbling occurred, and the cloudy white mixture was stirred at r.t. After 7 h., the reaction mixture was poured into an ice cold 0.1M NaOH solution (400 mL), and the aqueous solution was extracted with CH2Cl2 (2*200 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo to give a purple oil, which was purified by flash chromatography (SiO2, 0%-5% EtOAc/Hexanes) to give (3-Fluoro-5-methyl-phenyl)-dimethyl-amine as a yellow tinted oil (2.84 g, 58%).

Reference： [1]Patent: US2010/222325,2010,A1 .Location in patent: Page/Page column 123

11
[ 1296271-50-5 ]
[ 52215-41-5 ]
[ 1296270-55-7 ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 943 - 962

12
[ 1572-59-4 ]
[ 52215-41-5 ]
[ 1447640-64-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	In methanol; at 40℃; for 108h;	General procedure: A dry reaction vial containing a magnetic stir bar was charged with a-nitrodiazoesters (100 mg). To the vessel was added methanol (633 mul), followedimmediately by aniline (10 eq.). The reaction was allowed to stir at roomtemperature overnight. LCMS was used to monitor the reaction. When no 2-diazo-2-nitroacetate left, the mixture was immediately purified by flash column chromatography witha minimal amount of silica gel.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 4159 - 4163

13
[ 15431-30-8 ]
[ 52215-41-5 ]
[ 1447640-78-9 ]

Yield	Reaction Conditions	Operation in experiment
64%	In methanol; at 40℃; for 108h;	General procedure: A dry reaction vial containing a magnetic stir bar was charged with a-nitrodiazoesters (100 mg). To the vessel was added methanol (633 mul), followedimmediately by aniline (10 eq.). The reaction was allowed to stir at roomtemperature overnight. LCMS was used to monitor the reaction. When no 2-diazo-2-nitroacetate left, the mixture was immediately purified by flash column chromatography witha minimal amount of silica gel.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 4159 - 4163

14
[ 1442470-93-0 ]
[ 52215-41-5 ]
[ 1442473-64-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 80℃;	Example 72: A mixture of Example A47 (200 mg, 0.363 mmol), DIEA (188 mg,1.452 mmol) and 3-chloro-5-methylaniline (182 mg, 1.452 mmol) in dioxane (5 mL) washeated at 80C overnight. The mixture was cooled to RT, treated with EtOAc and satd.NaHC03 and the resulting solid collected via filtration and dried to afford crude 1-(4-chloro-5 -( 1-ethyl-7 -( ( 4-methoxybenzyl )(methyl )amino)-2-oxo-1 ,2-dihydro-1, 6-naphthyridin-3-yl )-2-fluorophenyl)-3-(3-fluoro-5-methylphenyl)urea (197 mg, 88% yield). MS (ESI) m/z: 618.2[M+Ht.

Reference： [1]Patent: WO2013/184119,2013,A1 .Location in patent: Paragraph 0329

15
[ 506-68-3 ]
[ 52215-41-5 ]
C₈H₇FN₂ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 8156 - 8162

16
[ 52215-41-5 ]
C₁₄H₁₁FN₂ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 8156 - 8162

17
[ 52215-41-5 ]
1-(3-fluoro-5-methylphenyl)-1,3-diphenylurea [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 8156 - 8162

18
[ 64-18-6 ]
[ 1245909-06-1 ]
2-azido-5-bromo-4-methylbenzaldehyde [ No CAS ]
[ 52215-41-5 ]
(2S)-2-[2-(2-azido-5-bromo-4-methylphenyl)-2-[(3-fluoro-5-methylphenyl)(formyl)amino]acetylamino]methyl}pyrrolidine-1-carboxylic acid benzyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; at 50℃;	to the mixture of 2-azido-5-bromo-4-methyl-benzaldehyde (360 mg, 1.5 mmol) and MeOH (10 mL) was added <strong>[52215-41-5]3-fluoro-5-methylaniline</strong> (0.19 mg, 1.5 mmol), formic acid (0.057 mL, 1.66 mmol) and 2-(S)-isocyanomethyl-pyrrolidine-l-carboxylic acid benzyl ester from Step 3-1 ( 0.55 g, 2.1 mmol). The resulting mixture was heated at 50 C overnight. The reaction solution was concentrated and dried under high vacuum to give brown solid as the desired product (70% pure). The crude material was used for next Step without further purification. MS (M+l)+: 639.2.

Reference： [1]Patent: WO2017/3724,2017,A1 .Location in patent: Paragraph 00221

19
6-chloro-8-(cyclopropyl(4-methoxybenzyl)amino)imidazo[1,2-b]pyridazine-3-carboxamide [ No CAS ]
[ 52215-41-5 ]
C₂₅H₂₅FN₆O₂ [ No CAS ]

Reference： [1]MedChemComm,2017,vol. 8,p. 700 - 712

20
6-chloro-8-((4-methoxybenzyl)(2,2,2-trifluoroethyl)amino)imidazo[1,2-b]pyridazine-3-carbonitrile [ No CAS ]
[ 52215-41-5 ]
6-((3-fluoro-5-methylphenyl)amino)-8-((4-methoxybenzyl)(2,2,2-trifluoroethyl)amino)imidazo[1,2-b]pyridazine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl acetamide; at 125℃; for 1h;Inert atmosphere; Sealed tube;	6-Chloro-8-((4-methoxybenzyl)(2,2,2-trifluoroethyl)amino)imidazo[l,2- b]pyridazine-3-carbonitrile (40 mg, 0.101 mmol) was dissolved in dimethylacetamide (0.9 mL). The vessel was purged with nitrogen for 15 minutes and then 3-fluoro-5- methylanihne (25.3 mg, 0.202 mmol), Pd2(dba)3 (9.26 mg, 10.11 muiotaetaomicron), Xantphos (11.70 mg, 0.020 mmol) and cesium carbonate (132 mg, 0.404 mmol) were added. The reaction vessel was sealed and heated at 125 C for 1 hour. The reaction was cooled to room temperature and diluted with ethyl acetate (200 mL). The solution was washed with water three times, and the organic layer dried over sodium sulfate. The slurry was filtered and concentrated to provide a crude product, which was then purified using automated chromatography, providing the intermediate product (22 mg, 46% yield). LC retention time 1.14 min [J]. MS (E+) m/z: 485 (MH+).

Reference： [1]Patent: WO2017/87590,2017,A1 .Location in patent: Page/Page column 78; 79

21
[ 1150566-27-0 ]
[ 52215-41-5 ]
ethyl 6-((3-fluoro-5-methylphenyl)amino)-3,8a-dihydroimidazo[1,2-b]pyridazine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl acetamide; at 125℃; for 1h;Inert atmosphere; Sealed tube;	Nitrogen was bubbled through a solution of ethyl 6-chloroimidazo[l,2- b]pyridazine-3-carboxylate (500 mg, 2.216 mmol) in dimethylacetamide (DMA, 5 mL) for 15 minutes and then <strong>[52215-41-5]3-fluoro-5-methylaniline</strong> (555 mg, 4.43 mmol) was added, followed by Pd2(dba)3 (203 mg, 0.222 mmol), Xantphos (256 mg, 0.443 mmol) and cesium carbonate (2888 mg, 8.86mmol). The reaction vessel was sealed and heated to 125 C for 1 hour. The reaction was cooled to room temperature and ethyl acetate and water were added. The suspension was filtered and the filtrate layers separated. The organic layer was dried over sodium sulfate, filtered, concentrated and purified using flash chromatography providing the coupling product (180 mg, 19% yield). LC retention time 1.95 min [O]. MS (E+) m/z: 315 (MH+).

Reference： [1]Patent: WO2017/87590,2017,A1 .Location in patent: Page/Page column 85; 86

22
[ 52215-41-5 ]
2-bromo-1-fluoro-5-iodo-3-methylbenzene [ No CAS ]

Reference： [1]Patent: US2018/72718,2018,A1
[2]Patent: US2018/72741,2018,A1
[3]Patent: US2018/72720,2018,A1
[4]Patent: US2019/76401,2019,A1

23
[ 52215-41-5 ]
2-bromo-1-fluoro-3-methyl-5-vinylbenzene [ No CAS ]

Reference： [1]Patent: US2018/72718,2018,A1
[2]Patent: US2018/72741,2018,A1
[3]Patent: US2018/72720,2018,A1
[4]Patent: US2019/76401,2019,A1

24
[ 52215-41-5 ]
4-bromo-3-fluoro-5-methyl benzaldehyde [ No CAS ]

Reference： [1]Patent: US2018/72718,2018,A1
[2]Patent: US2018/72741,2018,A1
[3]Patent: US2018/72720,2018,A1
[4]Patent: US2019/76401,2019,A1

25
[ 52215-41-5 ]
1-(4-bromo-3-fluoro-5-methylphenyl)-N-methylmethanamine [ No CAS ]

Reference： [1]Patent: US2018/72718,2018,A1
[2]Patent: US2018/72741,2018,A1
[3]Patent: US2018/72720,2018,A1
[4]Patent: US2019/76401,2019,A1

26
[ 52215-41-5 ]
tert-butyl 4-(4-bromo-3-fluoro-5-methylphenyl)-4-oxobutylcarbamate [ No CAS ]

Reference： [1]Patent: US2018/72741,2018,A1
[2]Patent: US2018/72720,2018,A1

27
[ 52215-41-5 ]
tert-butyl 2-(4-bromo-3-fluoro-5-methylphenyl)pyrrolidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2018/72741,2018,A1
[2]Patent: US2018/72720,2018,A1

28
[ 52215-41-5 ]
tert-butyl 6-(4-bromo-3-fluoro-5-methylphenyl)-3,4-dihydropyridine-1(2H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2018/72741,2018,A1
[2]Patent: US2018/72720,2018,A1

29
[ 52215-41-5 ]
tert-butyl 2-(4-bromo-3-fluoro-5-methylphenyl)piperidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2018/72741,2018,A1
[2]Patent: US2018/72720,2018,A1

30
[ 52215-41-5 ]
5-(2-fluoro-6-methyl-4-vinylphenyl)-3-(1-methyl-1H-pyrazol-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine [ No CAS ]

Reference： [1]Patent: US2018/72720,2018,A1

31
[ 52215-41-5 ]
3-fluoro-5-methyl-4-(3-(1-methyl-1H-pyrazol-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)benzaldehyde [ No CAS ]

Reference： [1]Patent: US2018/72720,2018,A1

32
[ 52215-41-5 ]
(3-fluoro-5-methyl-4-(3-(1-methyl-1H-pyrazol-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)phenyl)methanamine [ No CAS ]

Reference： [1]Patent: US2018/72720,2018,A1

33
[ 52215-41-5 ]
N-(3-fluoro-5-methyl-4-(3-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)benzyl)acetamide [ No CAS ]

Reference： [1]Patent: US2018/72720,2018,A1

34
[ 52215-41-5 ]
tert-butyl 3-fluoro-5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl(methyl)carbamate [ No CAS ]

Reference： [1]Patent: US2018/72718,2018,A1
[2]Patent: US2018/72741,2018,A1
[3]Patent: US2018/72720,2018,A1
[4]Patent: US2019/76401,2019,A1

35
[ 52215-41-5 ]
4-bromo-3-fluoro-5-methylaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 1.5h;	N-bromosuccinimide (15.8 g, 89 mmol) was added to a solution of <strong>[52215-41-5]3-fluoro-5-methylaniline</strong> (Combi-Blocks, 11 g, 88 mmol) in DMF (80 mL) cooled to 0 C. in an ice bath. The reaction mixture was stirred at 0 C. for 30 minutes. After warming to room temperature, the reaction was stirred for an additional 1 hour. Water and EtOAc were then added, and the separated organic phase was washed with saturated aqueous NaHCO3 and brine. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by Biotage Isolera (17.2 g, 96%). LCMS calculated for C7H8BrFN (M+H)+ m/z=203.9; found 204.0.
96%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 1.5h;	N-Bromosuccinimide (15.8 g, 89 mmol) was added to a solution of <strong>[52215-41-5]3-fluoro-5-methylaniline</strong> (Combi-Blocks, 11 g, 88 mmol) in DMF (80 mL) cooled to 0 C. in an ice bath. The reaction mixture was stirred at 0 C. for 30 minutes. After warming to r.t., the reaction was stirred for an additional 1 hour. Water and EtOAc were then added, and the organic phase was washed with saturated aqueous NaHCO3 and brine. The organic phase was then dried over magnesium sulfate and the solvents were evaporated under reduced pressure. The crude product was purified by Biotage Isolera (17.2 g, 96%). LCMS calculated for C7H8BrFN (M+H)+ m/z=203.9; found 204.0.
96%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 1.5h;	N-Bromosuccinimide (15.8 g, 89 mmol) was added to a solution of <strong>[52215-41-5]3-fluoro-5-methylaniline</strong> (Combi-Blocks, 11 g, 88 mmol) in DMF (80 mL) cooled to 0 C. in an ice bath. The reaction mixture was stirred at 0 C. for 30 minutes. After warming to r.t., the reaction was stirred for an additional 1 hour. Water and EtOAc were then added, and the organic phase was washed with saturated aqueous NaHCO3 and brine. The organic phase was then dried over magnesium sulfate and the solvents were evaporated under reduced pressure. The crude product was purified by Biotage Isolera (17.2 g, 96%). LCMS calculated for C7H8BrFN (M+H)+ m/z=203.9; found 204.0.

96%

With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0 - 20℃; for 1.5h;

N-Bromosuccinimide (15.8 g, 89 mmol) was added to a solution of <strong>[52215-41-5]3-fluoro-5-methylaniline</strong> (Combi-Blocks, 11 g, 88 mmol) in DMF (80 mL) cooled to 0 C. in an ice bath. The reaction mixture was stirred at 0 C. for 30 minutes. After warming to room temperature, the reaction was stirred for an additional 1 hour. Water and EtOAc were then added, and the organic phase was washed with saturated aqueous NaHCO3 and brine. The organic phase was then dried over magnesium sulfate and the solvents were evaporated under reduced pressure. The crude product was purified by Biotage Isolera (17.2 g, 96%). LCMS calculated for C7HsBrFN (M+H)+ m/z=203.9; found 204.0.

Reference： [1]Patent: US2018/72718,2018,A1 .Location in patent: Paragraph 0537; 0538
[2]Patent: US2018/72741,2018,A1 .Location in patent: Paragraph 0675-0676
[3]Patent: US2018/72720,2018,A1 .Location in patent: Paragraph 0823; 0824; 0825
[4]Patent: US2019/76401,2019,A1 .Location in patent: Paragraph 0355; 0356; 0357

36
[ 52215-41-5 ]
tert-butyl (4-bromo-3-fluoro-5-methylbenzyl)(methyl)carbamate [ No CAS ]

Reference： [1]Patent: US2018/72718,2018,A1
[2]Patent: US2018/72741,2018,A1
[3]Patent: US2018/72720,2018,A1
[4]Patent: US2019/76401,2019,A1

37
[ 52215-41-5 ]
tert-butyl 4-(6-cyano-1-trityl-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-fluoro-5-methylbenzyl(methyl)carbamate [ No CAS ]

Reference： [1]Patent: US2018/72718,2018,A1

38
[ 52215-41-5 ]
tert-butyl 4-(6-cyano-1H-pyrazolo[4,3-b]pyridin-5-yl)-3-fluoro-5-methylbenzyl(methyl)carbamate [ No CAS ]

Reference： [1]Patent: US2018/72718,2018,A1

39
[ 52215-41-5 ]
tert-butyl 5-(4-((tert-butoxycarbonyl(methyl)amino)methyl)-2-fluoro-6-methylphenyl)-6-cyano-3-iodo-1H-pyrazolo[4,3-b]pyridine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2018/72718,2018,A1

40
[ 52215-41-5 ]
5-(2-fluoro-6-methyl-4-((methylamino)methyl)phenyl)-3-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-b]pyridine-6-carbonitrile [ No CAS ]

Reference： [1]Patent: US2018/72718,2018,A1

41
[ 52215-41-5 ]
tert-butyl 5-(4-((tert-butoxycarbonyl(methyl)amino)methyl)-2-fluoro-6-methylphenyl)-1H-pyrazolo[4,3-d]pyrimidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2018/72741,2018,A1

42
[ 52215-41-5 ]
tert-butyl 3-fluoro-4-(3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-5-methylbenzyl(methyl)carbamate [ No CAS ]

Reference： [1]Patent: US2018/72741,2018,A1

43
[ 52215-41-5 ]
1-(3-fluoro-5-methyl-4-(3-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)-N-methylmethanamine [ No CAS ]

Reference： [1]Patent: US2018/72741,2018,A1

44
[ 52215-41-5 ]
2-(4-(5-(2-fluoro-6-methyl-4-((methylamino)methyl)phenyl)-1H-pyrazolo[4,3-d]pyrimidin-3-yl)-1H-pyrazol-1-yl)benzonitrile [ No CAS ]

Reference： [1]Patent: US2018/72741,2018,A1

45
[ 52215-41-5 ]
5-(2-fluoro-6-methyl-4-(pyrrolidin-2-yl)phenyl)-3-(4-(4-methylpiperazin-1-yl)phenyl)-1H-pyrazolo[4,3-d]pyrimidine [ No CAS ]

Reference： [1]Patent: US2018/72741,2018,A1

46
[ 52215-41-5 ]
C₂₃H₃₅BFNO₄ [ No CAS ]

Reference： [1]Patent: US2018/72741,2018,A1

Yield	Reaction Conditions	Operation in experiment
62%		General procedure: To a flame-dried 25 mL round bottom flask was charged activated Mg (7.5 mmol, 1.5 eq.) and 5 mL anhydrous THF. To this suspension was added 2 drops of 1,2-dibromoethane. After 5 min, a solution of Aryl bromide (5 mmol, 1.0 eq.) in 5 mL anhydrous THF was slowly added to the suspension of Mg at room temperature. The reaction was mildly exothermic. The Grignard reagent was titrated and 1 mmol of this reagent was added to a flame-dried reaction vial. The solution was diluted with 3 mL anhydrous toluene and after cooling to the target temperature T, a solution of oxaziridine (1.2 mmol, 1.2 eq.) in 1 mL anhydrous toluene was added. The reaction was maintained at the targeted temperature T for time t before being quenched with saturated aqueous NH4Cl. (The actual temperature/reaction time is listed for each substrate.)

48
[ 52215-41-5 ]
1-(5-(5-(2-fluoro-6-methyl-4-((methylamino)methyl)phenyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-ol [ No CAS ]

Reference： [1]Patent: US2018/72720,2018,A1

49
[ 52215-41-5 ]
tert-butyl 5-(4-((tert-butoxycarbonyl(methyl)amino)methyl)-2-fluoro-6-methylphenyl)-1H-pyrazolo[3,4-c]pyridine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2018/72720,2018,A1

50
[ 52215-41-5 ]
tert-butyl 5-(4-((tert-butoxycarbonyl(methyl)amino)methyl)-2-fluoro-6-methylphenyl)-3-iodo-1H-pyrazolo[3,4-c]pyridine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2018/72720,2018,A1

51
[ 52215-41-5 ]
tert-butyl 5-(4-((tert-butoxycarbonyl(methyl)amino)methyl)-2-fluoro-6-methylphenyl)-3-(6-chloropyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2018/72720,2018,A1

52
[ 52215-41-5 ]
1-(4-(3-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridin-5-yl)-3-fluoro-5-methylphenyl)-N-methylmethanamine [ No CAS ]

Reference： [1]Patent: US2018/72720,2018,A1

53
[ 52215-41-5 ]
C₁₉H₁₉FN₆*(x)C₂HF₃O₂ [ No CAS ]

Reference： [1]Patent: US2018/72720,2018,A1

54
[ 52215-41-5 ]
tert-butyl 2-(3-fluoro-5-methyl-4-(3-(1-methyl-1H-pyrazol-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)phenyl)pyrrolidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2018/72720,2018,A1

55
[ 52215-41-5 ]
tert-butyl 2-(3-fluoro-5-methyl-4-(3-(1-methyl-1H-pyrazol-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-5-yl)phenyl)piperidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: US2018/72720,2018,A1

56
[ 52215-41-5 ]
C₂₀H₂₁FN₆*(x)C₂HF₃O₂ [ No CAS ]

Reference： [1]Patent: US2018/72720,2018,A1

57
[ 893761-09-6 ]
[ 52215-41-5 ]
[ 1572509-84-2 ]