1262198-07-1|3-Bromo-2,6-difluoroaniline| Ambeed

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Quality Control of [ 1262198-07-1 ] Purity: 98% SDS Specification

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Product Details of [ 1262198-07-1 ]

CAS No. :	1262198-07-1
Formula :	C₆H₄BrF₂N
M.W :	208.00
SMILES Code :	NC1=C(F)C=CC(Br)=C1F
MDL No. :	MFCD22627833
Boiling Point :	No data available
InChI Key :	HIZADWSSPWORHH-UHFFFAOYSA-N
Pubchem ID :	21645692

Safety of [ 1262198-07-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340-P405-P501

Application In Synthesis of [ 1262198-07-1 ]

* 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.

Downstream synthetic route of [ 1262198-07-1 ]

[ 1262198-07-1 ] Synthesis Path-Downstream 1~36

Yield	Reaction Conditions	Operation in experiment
425 mg (63%)		Step 3. Preparation of 3-bromo-2,6-difluoroaniline To a round bottom flask containing tert-butyl 3-bromo-2,6-difluorophenylcarbamate (1 g, 3.3 mmol) was added DCM (3 mL) and TFA (3 mL). The reaction was stirred for 2 hours at room temperature. The volatiles were removed in vacuo, and the resulting residue was neutralized with saturated aqueous NaHCO3 solution to pH 8. The aqueous mixture was extracted with EtOAc. Organic phase was washed with water, brine, dried (Na2SO4), filtered and concentrated onto silica. Purification by flash chromatography (SiO2; 0-50% EtOAc in heptane) afforded 425 mg (63%) of 3-bromo-2,6-difluoroaniline: LCMS(m/z) 208.0 (MH+); tR=0.80 minute; 1H NMR (400 MHz, DMSO-d6) δ 5.54 (s, 2H) 6.78 (ddd, J=9.0, 7.4, 5.5 Hz, 1H) 6.85-6.95 (m, 1H).

2
PD₂ [ No CAS ]
bis(pinacolato)diboron [ No CAS ]
[ 1262198-07-1 ]
[ 1269233-07-9 ]
[ 2622-14-2 ]
[ 1269233-08-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate; In 1,4-dioxane;	Step 5. Preparation of N-(2,6-difluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propane-1-sulfonamide (SM-14) The mixture of <strong>[1262198-07-1]3-bromo-2,6-difluoroaniline</strong> and N-(3-bromo-2,6-difluorophenyl) propane-1-sulfonamide (560 mg, 2.69 mmol) was combined with bis(pinacolato)diboron (820 mg, 3.23 mmol), tricyclohexylphosphine (52.8 mg, 0.188 mmol), potassium acetate (396 mg, 4.04 mmol), and Pd2 dba3 (74.0 mg, 0.081 mmol) in 1,4-dioxane (10 mL) to give a yellow suspension. The reaction mixture was heated in a oil bath to 120 C. for 2 hours whereupon LCMS indicated complete conversion. The reaction was allowed to cool to room temperature and partitioned between EtOAc and water. The layers were separated and the aqueous portion was extracted with EtOAc. The combine organic portions were washed with water (2*), brine, dried (Na2SO4), and concentrated to give a dark brown oil as a mixture of boronate esters which was used without further purification: N-(2,6-difluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propane-1-sulfonamide LCMS(m/z) 174.0 (MH+, boronic acid); tR=0.33 minute.

References: [1]Patent: US2011/52578,2011,A1 .

3
[ 10147-36-1 ]
[ 1262198-07-1 ]
[ 1269233-07-9 ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine;	Step 4. Preparation of N-(3-bromo-2,6-difluorophenyl) propane-1-sulfonamide To a solution of <strong>[1262198-07-1]3-bromo-2,6-difluoroaniline</strong> (425 mg, 2.04 mmol) in dry pyridine (2.0 mL) was added 1-propanesulfonyl chloride (275 μL, 2.45 mmol) and the resulting reaction was maintained overnight at room temperature. The reaction was partitioned between EtOAc and water, and the layers separated. The aqueous portion was extracted with EtOAc and the combined organic portions were washed with 10% aqueous citric acid solution, water, brine, dried (Na2SO4), and concentrated to yield a brown viscous oil as a 2:1 mixture of <strong>[1262198-07-1]3-bromo-2,6-difluoroaniline</strong> and N-(3-bromo-2,6-difluorophenyl) propane-1-sulfonamide which was carried forward without further purification: N-(3-bromo-2,6-difluorophenyl) propane-1-sulfonamide LCMS(m/z) not ionized (MH+); tR=1.06 minutes.

References: [1]Patent: US2011/52578,2011,A1 .

4
[ 3896-29-5 ]
[ 1262198-07-1 ]

Yield	Reaction Conditions	Operation in experiment
73%	With N-Bromosuccinimide; sulfuric acid; at 20℃;	N-(2,6-difluorophenyl)acetamide (2, 8.77 g, 51.2 mmol) was dissolved in Sulfuric acid (41.0 mL, 769 mmol) and N-bromosuccinimide (9.12 g, 51.2 mmol) was added portion wise at rt. The reaction was stirred overnight at RT and quenched slowly into ice water (400 mL) with stirring. The solids were collected by suction filtration and washed with water, hexane, hexane + EtOAc (8+2) and hexane again. The solids were taken up in ethanol (30.0 mL) and conc. HCl (30 mL) and heated to reflux for 3h. The mixture was poured into ice (400 g), neutralized with solid NaOH and the solids were collected by suction filtration, washed with water and dried in vacuo to yield 3-bromo-2,6-difluoroaniline (3, 7.83 g, 37,6 mmol, 73% yield). (0997) Analytical data: (0998) 1H NMR (200 MHz, CDCl3) δ 6.95- 6.59 (m, 2H), 3.84 (s, 2H); (0999) 13C NMR (50 MHz, CDCl3) δ 152.2 (dd, J = 133.8, 6.5 Hz), 147.5 (dd, J = 132.7, 6.9 Hz), 125.4 (t, J = 16.9 Hz), 122, 119.6 (d, J = 8.4 Hz), 111.7 (dd, J = 19.9, 3.1 Hz), 103.8 (dd, J = 19.2, 3.8 Hz).
	With N-Bromosuccinimide; sulfuric acid; trifluoroacetic acid; at 20℃;	2,6-difluoro-acetanilide (3.02 g, 17.3 mmol) is taken-up in TFA (15 mL) and conc. H2SO4 (20 mL). NBS (3.20 g, 17.9 mmol) is added in small portions and the resulting mixture is stirred at rt overnight. The reaction mixture is poured into ice water and the resulting precipitate is collected by filtration, washed with H2O and dried in vacuo to give the bromide IM-1a (HPLC-MS: tRet.=0.79 min; MS (M+H)+=250/252) which is used without further purification

References: [1]Patent: WO2019/149738,2019,A1 .Location in patent: Page/Page column 96; 97; 98.
[2]Patent: WO2012/85127,2012,A1 .
[3]Patent: US2012/322803,2012,A1 .Location in patent: Page/Page column 18.
[4]Patent: WO2018/152107,2018,A1 .

5
[ 1262198-07-1 ]
[ 1383745-30-9 ]

Yield	Reaction Conditions	Operation in experiment
		C.1. Synthesis of azides B-1 C.1.1. Experimental procedure for the synthesis of B1 -a SM-2a B-1 aThe aniline SM-2a (2.66 g, 12.8 mmol) is suspended in TFA (60 mL) and cooled to 0 C. NaN02 (1.39 g, 20.1 mmol) is added and the mixture stirred for 30 min. NaN3 (1.06 g, 16.2 mmol) is slowly added at 0 C and the mixture is stirred for additional 60 min. Et20 (25 mL) is added dropwise, the cooling bath is removed and the reaction mixture is allowed to warm to rt. H20 is added and the mixture is extracted 3 x with Et20. The combined organic layer is dried over MgS04, filtered and evaporated to yield the azide B-1 a which is used without further purification.
		The aniline SM-2a (2.66 g, 12.8 mmol) is suspended in TFA (60 mL) and cooled to 0 C. NaNO2 (1.39 g, 20.1 mmol) is added and the mixture stirred for 30 min. NaN3 (1.06 g, 16.2 mmol) is slowly added at 0 C. and the mixture is stirred for additional 60 min. Et2O (25 mL) is added dropwise, the cooling bath is removed and the reaction mixture is allowed to warm to rt. H2O is added and the mixture is extracted 3× with Et2O. The combined organic layer is dried over MgSO4, filtered and evaporated to yield the azide B-1a which is used without further purification

References: [1]Patent: WO2012/85127,2012,A1 .Location in patent: Page/Page column 74.
[2]Patent: US2012/322803,2012,A1 .Location in patent: Page/Page column 55.

6
[ 1262198-07-1 ]
[ 1383745-32-1 ]

References: [1]Patent: WO2012/85127,2012,A1 .
[2]Patent: US2012/322803,2012,A1 .

7
[ 1262198-07-1 ]
[ 1383745-39-8 ]

References: [1]Patent: WO2012/85127,2012,A1 .
[2]Patent: US2012/322803,2012,A1 .

8
[ 1262198-07-1 ]
[ 1383745-34-3 ]

References: [1]Patent: WO2012/85127,2012,A1 .
[2]Patent: US2012/322803,2012,A1 .

9
[ 1262198-07-1 ]
[ 1383744-99-7 ]

References: [1]Patent: WO2012/85127,2012,A1 .
[2]Patent: US2012/322803,2012,A1 .

10
[ 1383745-09-2 ]
[ 1262198-07-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; In ethanol; at 70℃; for 18h;	Step 2 The bromide IM-1 a (3.60 g, 14.4 mmol) is taken-up in EtOH (10 mL), cone. HCI (10 mL) is added and the mixture stirred at 70 C for 18 h. After cooling to rt EtOH is evaporated whereupon a precipitate is formed which is collected by filtration and air-dried to give aniline SM-2a (HPLC-MS: tRet. = 1.1 1 min; MS (M+H)+ = 208/210) which is used without further purification.
	With hydrogenchloride; In ethanol; at 70℃; for 18h;	The bromide IM-1a (3.60 g, 14.4 mmol) is taken-up in EtOH (10 mL), conc. HCl (10 mL) is added and the mixture stirred at 70 C. for 18 h. After cooling to rt EtOH is evaporated whereupon a precipitate is formed which is collected by filtration and air-dried to give aniline SM-2a (HPLC-MS: tRet.=1.11 min; MS (M+H)+=208/210) which is used without further purification.
	With hydrogenchloride; In ethanol; at 75℃;	To a solution of N-(3-bromo-2,6-difluorophenyl)acetamide in EtCH (5.7 mL) was added concentrated HCI (5.7 mL) at room temperature. The reaction mixture was allowed to stir overnight at 75 C. Upon completion, the reaction mixture was cooled to room temperature. The reaction mixture was cooled to 0 C and basified with aqueous NaCH solution. The reaction mixture was extracted three times with EtOAc. The combined organic layers were dried with anhydrous Na2SO4 and concentrated in vacuo to give 3-bromo- 2,6- difluoroaniline, which was used in the next step without further purification.

References: [1]Patent: WO2012/85127,2012,A1 .Location in patent: Page/Page column 40.
[2]Patent: US2012/322803,2012,A1 .Location in patent: Page/Page column 18.
[3]Patent: WO2018/152107,2018,A1 .Location in patent: Page/Page column 23.

11
[ 1262198-07-1 ]
[ 74-88-4 ]
3-bromo-2,6-difluoro-N,N-dimethylaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
411 mg	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; for 0.666667h;	To a solution of <strong>[1262198-07-1]3-bromo-2,6-difluoroaniline</strong> (279 mg, 1.34 mmol) in dry N,Ndimethylformamide (10 mL) were added iodomethane (952 mg, 6.71 mmol, 0.4 mL) and sodium hydride (268 mg, 6.71 mmol; 60% in mineral oil). After stirring for 40 mm, the reactionmixture was quenched with water (40 mL). The resulting mixture was extracted with diethyl ether (2x40 mL). The combined organic layers were washed with water (2x20 mL) and brine (2x20 mL), dried with sodium sulfate and concentrated in vacuo to afford 411 mg (>100% yield) of 3-Bromo-2,6-difluoro-N,N-dimethylaniline with a purity of 99% according to LC-MS. The material was used as such.LC-MS (Method Li): R1 = 2.21 mm; m/z = 236/238 (M+H)

References: [1]Patent: WO2017/178416,2017,A1 .Location in patent: Page/Page column 120; 121.

12
[ 5509-65-9 ]
[ 1262198-07-1 ]

References: [1]Patent: WO2018/152107,2018,A1 .
[2]Patent: WO2019/149738,2019,A1 .

13
[ 1262198-07-1 ]
[ 1314734-58-1 ]
(3-amino-2,4-difluorophenyl)-[5-bromo-1-(oxan-2-yl)pyrazolo[3,4-b]pyridin-3-yl]methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%		To <strong>[1262198-07-1]3-bromo-2,6-difluoroaniline</strong> (4.69 g, 22.6 mmol) in tetrahydrofuran (19.6 mL) was added 2M isopropylmagnesium chloride in THF (11.3 mL, 22.6 mmol) dropwise at 0 C and stirred for 15 minutes without further cooling. After cooling again to 0C, chlorotrimethylsilane (2.86 mL, 22.6 mmol) was added, the mixture warmed to 25 C and stirred for 20 minutes. The solution was cooled to 0C and chlorotrimethylsilane (2.86 mL, 22.6 mmol) was added stirring continued for 20 minutes at 25 C. The solution was cooled to 0C again and 2M isopropylmagnesium chloride in THF (11.3 mL, 22.6 mmol) was added dropwise and the mixture was stirred for 10 minutes at 0C.5-bromo-N-methoxy-N-methyl-1-(oxan-2-yl)pyrazolo[3,4-b]pyridine-3-carboxamide (3.62 g, 9.80 mmol) was dissolved in 10 mL THF and added to the mixture and stirring was continued for 1h at RT. The reaction was quenched with sat. NH4Cl solution, water was added until the aqueous phase became clear and the phases were separated. The aqueous was extracted with EtOAc, the extracts were washed with brine, dried over Na2SO4 and the solvent was removed. The oily residue was dissolved in 25 mL THF and 2 mL conc. HCl were added with stirring. After 5 minutes, the mixture was carefully neutralized with solid K2CO3, diluted with EtOAc and filtered. The solvents were removed and the residue purified by flash chromatography (n-hexane / EtOAc gradient, from 0% to 40% EtOAc) to yield (3-amino-2,4-difluorophenyl)-[5-bromo-1-(oxan-2-yl)pyrazolo[3,4-b]pyridin-3-yl]methanone (2.35 g, 5,37 mmol, 55% yield). (1142) Analytical data: (1143) 1H NMR (200 MHz, DMSO) δ 8.76 (dd, J = 13.9, 2.1 Hz, 2H), 7.15- 6.89 (m, 2H), 6.12 (d, J = 7.8 Hz, 1H), 5.51 (s, 2H), 4.08- 3.56 (m, 2H), 2.46- 2.20 (m, 1H), 2.06- 1.46 (m, 5H). 13C NMR (50 MHz, DMSO) δ 185.6, 153.6 (dd, J = 190, 9 Hz), 150.6, 149.0,146.8 (d, J = 9 Hz), 140.2, 133.0, 126.3 (t, J = 17 Hz), 122.3 (dd, J = 11, 3 Hz), 116.4 (d, J = 3 Hz), 116.2, 116.2, 115.7, 110.7 (dd, J = 19, 3 Hz), 82.7, 67.0, 28.5, 24.4, 21.8. MS: [M+Na+MeOH]+ = 491.05.

References: [1]Patent: WO2019/149738,2019,A1 .Location in patent: Page/Page column 118; 119.

14
[ 1262198-07-1 ]
N-[3-(5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carbonyl)-2,6-difluorophenyl]methanesulfonamide [ No CAS ]