1206800-24-9|6-Bromo-5-(2-fluoro-4-nitrophenoxy)-1-methyl-1H-indazole| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 1206800-24-9 ] Purity: 95% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 1206800-24-9 ]

CAS No. :	1206800-24-9
Formula :	C₁₄H₉BrFN₃O₃
M.W :	366.14
SMILES Code :	CN1N=CC2=C1C=C(Br)C(OC3=CC=C([N+]([O-])=O)C=C3F)=C2
MDL No. :	MFCD17169897
InChI Key :	PVURLVXVVVMHMW-UHFFFAOYSA-N
Pubchem ID :	66766853

Safety of [ 1206800-24-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 1206800-24-9 ]

* 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 [ 1206800-24-9 ]
Downstream synthetic route of [ 1206800-24-9 ]

[ 1206800-24-9 ] Synthesis Path-Upstream 1~17

1
[ 1206800-26-1 ]
[ 1206800-24-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6.5 h; Inert atmosphere	1-(2,4-Dibromo-5-(2-fluoro-4-nitrophenoxy)benzylidene)-2-methylhydrazine (1.0 g, 2.2 mmol), cuprous chloride (22 mg, 0.2 mmol), potassium carbonate (0.638 g, 7.2 mmol), DMF (10 mL), and a stir bar are combined in a pressure tube under nitrogen. The cap is sealed and the tube is placed in an oil bath with stirring. The bath is heated to 100° C. over 30 min and held at 100° C. for 6 hours and then cooled to RT. The reaction mixture is poured into a separatory funnel containing MTBE (10 mL) and water (10 mL). The layers are separated and the aqueous layer is extracted with an additional portion of MTBE (10 mL). The organic layers are combined, and washed with water followed by saturated sodium chloride aqueous solution. The organic layer is dried over magnesium sulfate and concentrated to yield 0.70 g of crude product. The crude solid is dissolved in DCM and heptane, and then concentrated to remove DCM resulting in the formation of a slurry. The product is collected by filtration and dried under vacuum to give 6-bromo-5-(2-fluoro-4-nitrophenoxy)-1-methyl-1H-indazole as a solid (0.65 g, 79percent yield). MS (m/z): 367.8 (M+H).

References: [1] Patent: US2010/22529, 2010, A1, . Location in patent: Page/Page column 5.
[2] Organic Process Research and Development, 2014, vol. 18, # 4, p. 501 - 510.

2
[ 1206800-19-2 ]
[ 74-88-4 ]
[ 1206800-24-9 ]
[ 1206801-13-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydrogencarbonate; potassium carbonate In N,N-dimethyl-formamide at 4.5 - 20℃;	Preparation 100 6-Bromo-5-(2-fluoro-4-nitrophenoxy)-1-methyl-i H-indazole To a 4000 mL flask is added 6-bromo-5-(2-fluoro-4-nitrophenoxy)-1H-indazole (230 g, 653.2 mmol), DMF (3000 mL), and K₂CO₃ (135.41 g, 979.78 mmol). The reaction mixture is cooled to 4.5° C. with an ice bath. To the mixture is added methyl iodide (92.71 g, 653.19 mmol) and the reaction is allowed to stir for 20 min at the same temperature. The reaction is allowed to warm to RT and stir for 13 hours. The reaction mixture is monitored by liquid chromatography mass spectrometry. Additional methyl iodide (50 g) and NaHCO₃ (33 g) are added and the reaction mixture is stirred at RT until the reaction is completed. The reaction mixture is divided into two portions labeled (A) and (B), and each one is quenched with water (1 L) followed by extraction with EtOAc (1 L) causing some solids to form. The combined solids from (A) and (B) are collected by vacuum filtration to give 70 g of crude weight having about 90percent 6-bromo-5-(2-fluoro-4-nitrophenoxy)-1-methyl-1H-indazole (which is the desired isomer) and 8percent 6-bromo-5-(2-fluoro-4-nitrophenoxy)-2-methyl-2H-indazole isomers. This solid is then triturated with 1000 mL of DCM and 750 mL of MeOH overnight (about 14 hours). The solid is collected by filtration and rinsed with fresh DCM (100 mL) to give 55.5 g of desired material labeled (C). The mother liquor is concentrated and labeled (D). The organic layer from (A) and (B) are separated and concentrated. The residues from (A) and (B) are combined to give 185 g of crude as an orange solid labeled (E). The crude compound (E) is dissolved in MeOH and DCM, and then the solution is divided into 3 portions. 600 g of silica gel is mixed with each portion of solution, and then the silica gel mixture is loaded into seven 270 g size empty cartridges. Seven 1.5 kg ISCO.(R). columns are used with solvent system starting with 25percent EtOAc in hexanes, then it is switched to 50percent EtOAc in hexanes to give 62 g of the desired compound as a yellow powder labeled (F). After 7 runs, there are some mixed fractions of 6-bromo-5-(2-fluoro-4-nitrophenoxy)-1-methyl-1H-indazole and 6-bromo-5-(2-fluoro-4-nitrophenoxy)-2-methyl-2H-indazole isomers. The fractions are combined and combined with mother liquor (D) from the procedure described above to give 17 g of the mixture. The mixture is dissolved in MeOH and DCM, mixed with 170 g of silica into the solution, and run on a 1.5 kg column to give 10 g of a yellow powder as the desired product labeled (G). Total yield (55.5 g (C), 62 g (F), and 10 g (G)) is 127.5 g.

References: [1] Patent: US2010/22529, 2010, A1, . Location in patent: Page/Page column 13-14.
[2] Organic Process Research and Development, 2014, vol. 18, # 4, p. 501 - 510.

3
[ 369-34-6 ]
[ 1403767-19-0 ]
[ 1206800-24-9 ]

References: [1] Organic Process Research and Development, 2014, vol. 18, # 4, p. 501 - 510.
[2] Organic Process Research and Development, 2018, vol. 22, # 3, p. 409 - 419.

4
[ 102-50-1 ]
[ 1206800-24-9 ]

References: [1] Organic Process Research and Development, 2014, vol. 18, # 4, p. 501 - 510.
[2] Organic Process Research and Development, 2014, vol. 18, # 4, p. 501 - 510.

5
[ 31601-41-9 ]
[ 1206800-24-9 ]

References: [1] Organic Process Research and Development, 2014, vol. 18, # 4, p. 501 - 510.
[2] Organic Process Research and Development, 2014, vol. 18, # 4, p. 501 - 510.

6
[ 861084-04-0 ]
[ 1206800-24-9 ]

References: [1] Organic Process Research and Development, 2014, vol. 18, # 4, p. 501 - 510.
[2] Organic Process Research and Development, 2014, vol. 18, # 4, p. 501 - 510.

7
[ 1206800-17-0 ]
[ 1206800-24-9 ]

References: [1] Organic Process Research and Development, 2014, vol. 18, # 4, p. 501 - 510.
[2] Organic Process Research and Development, 2014, vol. 18, # 4, p. 501 - 510.

8
[ 57848-46-1 ]
[ 1206800-24-9 ]

References: [1] Organic Process Research and Development, 2018, vol. 22, # 3, p. 409 - 419.
[2] Organic Process Research and Development, 2018, vol. 22, # 3, p. 409 - 419.

9
[ 679839-39-5 ]
[ 1206800-24-9 ]

References: [1] Organic Process Research and Development, 2018, vol. 22, # 3, p. 409 - 419.
[2] Organic Process Research and Development, 2018, vol. 22, # 3, p. 409 - 419.

10
[ 1577179-97-5 ]
[ 1206800-24-9 ]