[ CAS No. 1427382-02-2 ] {[proInfo.proName]}

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Quality Control of [ 1427382-02-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1427382-02-2 ]

SDS Specification

Alternatived Products of [ 1427382-02-2 ]

Product Details of [ 1427382-02-2 ]

CAS No. :	1427382-02-2	MDL No. :	MFCD23712061
Formula :	C₈H₆BrFO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	233.03	Pubchem ID :	-
Synonyms :

Safety of [ 1427382-02-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1427382-02-2 ]

* 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 [ 1427382-02-2 ]

[ 1427382-02-2 ] Synthesis Path-Downstream 1~52

1
[ 124-38-9 ]
[ 51437-00-4 ]
[ 1427382-02-2 ]

Yield	Reaction Conditions	Operation in experiment
52%		To a solution of 4-bromo-1-fluoro-2-methylbenzene (5.0 g, 26.4 mmol) in THF was added dropwise LDA (2 M in THF, 29.0 mmol) at -65 C under N2 atmosphere. The resulting mixture was stirred at -65 C for 2 h, after which excess solid carbon dioxide was added. The mixture was stirred for 30 mm and warmed to room temperature. The reaction mixture was diluted with water (50 mL) and extracted with EtOAc (50 mL x 2). The aqueous layer was acidified to pH 3 by 2 M HC1 and extracted with EtOAc (50 mL x 2). The combined organic layers were washed with brine (50 mL), dried over Na2SO4 and concentrated to give 5-bromo-2-fluoro-3-methylbenzoic acid (3.4 g, 52%), which was used for the next step without further purification. 1H NMR (400 MHz, DMSO-d6) (ppm): 13.47 (s, 1H), 7.75 (d, J 6.0 Hz, 2H), 2.26 (d, J 1.6 Hz, 3H).
21%		To a solution of diisopropylamine (1.77g, 17.5 mmol, 1.1 eq) in THF (20 mL) was added n-BuLi (7.3 mL, 2.4 M in THF, 17.5 mmol, 1.1 eq) at -78C under N2. The mixture was stirred at -78C for lh, then a solution of 4-bromo-l-fluoro-2 -methyl-benzene (3 g, 15.8 mmol, 1.0 eq ) in THF (20 mL) was added dropwise. The reaction was stirred a further 2h at -78C then C02 gas was bubbled into the mixture for 30 min. The reaction was quenched by addition of water and acidified to pH 3 by addition of 1M HCl. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with brine, dried (Na2S04), filtered and evaporated in vacuo. The residue obtained was purified by chromatography to give the title compound as a white solid (697 mg, 21 %).LC-MS : m/z 230.9, 232.9 [M-H]" HNMR (400 MHz, DMSO-d6) ? 7.94 - 7.59 (m, 2H), 2.26 (s, 3H)

Reference： [1]Patent: WO2018/102419,2018,A1 .Location in patent: Paragraph 0312; 0313; 0314; 0315
[2]Patent: WO2013/37705,2013,A2 .Location in patent: Page/Page column 71; 72

2
[ 1427382-02-2 ]
[ 768-35-4 ]
[ 1427406-90-3 ]

Yield	Reaction Conditions	Operation in experiment
73%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; at 85℃;	To a solution of <strong>[1427382-02-2]5-bromo-2-fluoro-3-methyl-benzoic acid</strong> (697 mg, 2.99 mmol, 1.0 eq) and (3-fluorophenyl)boronic acid (502 mg, 3.59 mmol, 1.2 eq) in a mixture of EtOH (10 mL), dioxane (20 mL) and H20 (10 mL) were added K2C03 (142 mg, 1.03 mmol, 2.5 eq) and Pd(PPh3)4 (345 mg, 0.30 mmol, 0.1 eq). The mixture was heated at 85C overnight. The reaction was quenched by addition of 1 M HCl and the aqueous phase extracted with EtOAc. The organic extract was dried (MgSC^), filtered and evaporated in vacuo. The residue was purified by chromatography to give the title compound as a solid (558 mg, 73 %). LC-MS : m z 247.0 [M-H]~ 'H NMR (400 MHz, DMSO-de) ? 7.95 - 7.86 (m, 2H), 7.58 - 7.47 (m, 3H), 7.27 - 7.18 (m, 1H), 2.34 (d, J = 1.9 Hz, 3H)

Reference： [1]Patent: WO2013/37705,2013,A2 .Location in patent: Page/Page column 72

3
[ 13331-23-2 ]
[ 1427382-02-2 ]
2-fluoro-5-(furan-2-yl)-3-methylbenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,4-dioxane; water; at 80℃; for 0.5h;Inert atmosphere; Microwave irradiation;	To a degassed souDon of 9:1 1 ,4-doxane:H2O (4 mL) was added 5-bromo-2-fiuoro-3-methybenzoc acid (M4) (0.200 g, 0.858 mmo), 2-furanboronc acid (0.106 g, 0.944 mmo),K2003 (0.178 g, 1.287 mmo) and PdC2(PPh3)2 (0.030 g, 0.043 mmo), under an atmosphere of ntrogen. The reaction was rradated n a CEM microwave reactor at 80 C for 30 mn, then cooed and passed through a pad of Cehte. The Cehte was washed with EtOAc (20 mL). The mixture was acdfied using 2 M HC (1 mL) and concentrated n vacuo.The crude matera was purfied by sWca g& chromatography (soera Botage, 24 g S Cartridge, 0-60% EtOAc n petroeum benzne 40-60 C). Fractions contanng the suspected product were concentrated n vacuo to give 2-fuoro-5-(furan-2-y)-3-methythenzoc acid (M 5) (0.050 g, 26 % yed) as a white sohd. LCMS B rt. 3.63 mn, m/z 221 .1 [M+H].

Reference： [1]Patent: WO2016/198507,2016,A1 .Location in patent: Page/Page column 58; 59
[2]Journal of Medicinal Chemistry,2020,vol. 63,p. 4655 - 4684

4
[ 1427382-02-2 ]
tert-butyl 3-((2-(4-fluoro-5-methyl-[1,1‘-biphenyl]-3-carbonyl)hydrazinyl)sulfonyl)pyrrolidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/102419,2018,A1

5
[ 1427382-02-2 ]
tert-butyl 3-((2-(4-fluoro-5-methyl-[1,1‘-biphenyl]-3-carbonyl)hydrazinyl)sulfonyl)azetidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/102419,2018,A1

6
[ 1427382-02-2 ]
benzyl 3-((2-(4-fluoro-5-methyl-[1,1‘-biphenyl]-3-carbonyl)hydrazinyl)sulfonyl)azetidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/102419,2018,A1

7
[ 1427382-02-2 ]
C₁₅H₁₅FN₂O₃S [ No CAS ]

Reference： [1]Patent: WO2018/102419,2018,A1

8
[ 1427382-02-2 ]
C₁₆H₁₇FN₂O₃S [ No CAS ]

Reference： [1]Patent: WO2018/102419,2018,A1

9
[ 1427382-02-2 ]
4-fluoro-5-methyl-[1,1’-biphenyl]-3-carbohydrazide [ No CAS ]

Reference： [1]Patent: WO2018/102419,2018,A1

10
[ 1427382-02-2 ]
[ 98-80-6 ]
4-fluoro-5-methyl-[1,1’-biphenyl]-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 6h;Inert atmosphere;	To a mixture of <strong>[1427382-02-2]5-bromo-2-fluoro-3-methylbenzoic acid</strong> (3.5 g, 15.0 mmol) and phenylboronic acid (2.19 g, 18.0 mmol) in dioxane/water (60 mL, 5:1) were added PdC12(dppf)2 (1.09 g, 1.50 mmol) and potassium carbonate (8.29 g, 60.0 mmol) at room temperature under N2 atmosphere. After heating at 90 C for 6 h, the reaction mixture was poured into 1 M HC1 solution and extracted with EA (150 mL x 2). The combined organic layers were washed with 1 M HC1 (100 mL x 2), water (100 mL) and brine (100 mL), dried over Na2SO4 and concentrated. The residue was recrystallized from hexane to give 4-fluoro- 5-methyl-[1,1?-biphenyl]-3-carboxylic acid (3 g, 82%) as a yellow solid.LC-MS (Agilent): R 3.51 mm; m/z calculated for C14H11F02 [M-H] 229.1, found 229.1; 1H NMR (400 MHz, CDC13) (ppm): 8.06 (d, J = 6.0 Hz, 1H), 7.64 (d, J = 6.0 Hz, 1H), 7.57 (d, J= 7.6 Hz, 2H), 7.45 (t, J= 7.6 Hz, 2H), 7.37 (t, J 7.2 Hz, 1H), 2.40 (s, 3H).

Reference： [1]Patent: WO2018/102419,2018,A1 .Location in patent: Paragraph 0312; 0316; 0317; 0318; 0319

11
[ 1427382-02-2 ]
C₁₇H₁₇FN₂O₄S [ No CAS ]