1254123-51-7|5-Bromo-3-(difluoromethyl)-2-methoxypyridine| Ambeed

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Quality Control of [ 1254123-51-7 ] Purity: 95% SDS Specification

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Product Details of [ 1254123-51-7 ]

CAS No. :	1254123-51-7
Formula :	C₇H₆BrF₂NO
M.W :	238.03
SMILES Code :	COC1=NC=C(Br)C=C1C(F)F
MDL No. :	MFCD23163928
InChI Key :	AJNHTTUMXPNNAH-UHFFFAOYSA-N
Pubchem ID :	67979709

Safety of [ 1254123-51-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H320-H335
Precautionary Statements:	P264-P270-P301+P312-P330

Application In Synthesis of [ 1254123-51-7 ]

* 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 [ 1254123-51-7 ]

[ 1254123-51-7 ] Synthesis Path-Downstream 1~21

1
[ 1254123-51-7 ]
[ 1383847-34-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogen bromide; acetic acid; at 20 - 50℃; for 6.66667h;	Example 23i 5-Bromo-3-(difluoromethyl)pyridin-2(1H)-one Hydrobromic acid (33% in glacial acetic acid) (63.4 mL, 361 mmol) was added to <strong>[1254123-51-7]5-bromo-3-(difluoromethyl)-2-methoxypyridine</strong> (6.37 g, 26.8 mmol, Example 22i). The resulting reaction mixture was stirred at r.t. for 5 h, then at 40 C. for 75 min, then at 50 C. for 25 min. The reaction was allowed to cool, then the reaction mixture was concentrated in vacuo. The residue was partitioned between NaHCO3 (aq. sat.) and CHCl3. The aqueous phase was extracted twice with CHCl3, the combined organics were passed through a phase separator and concentrated to give the title compound (5.68 g, 95% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 6.81 (t, 1H), 7.78-7.83 (m, 1H), 7.89 (m, 1H), 12.46 (br. s., 1H); MS (ES+) m/z 224 [M+H]+.

References: [1]Patent: US2012/165346,2012,A1 .Location in patent: Page/Page column 18.

2
[ 103058-87-3 ]
[ 1254123-51-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With diethylamino-sulfur trifluoride; In dichloromethane; at 0 - 25℃; for 72h;Inert atmosphere;	Example 22i 5-Bromo-3-(difluoromethyl)-2-methoxypyridine To <strong>[103058-87-3]5-bromo-2-methoxynicotinaldehyde</strong> (5 g, 23 mmol) in dry CH2Cl2 (100 mL) at 0 C. under argon was diethylaminosulphur trifluoride (3.69 mL, 30.1 mmol) added over 1 min. The reaction mixture was stirred for three days while the reaction warmed to r.t. The reaction was quenched by the addition of sat. aqueous sodium bicarbonate solution. The reaction mixture was combined with another reaction based on <strong>[103058-87-3]5-bromo-2-methoxynicotinaldehyde</strong> (100 mg, 0.46 mmol) prior to workup. The phases were separated and the water phase was further extracted with CH2Cl2 (x 3). The organic layers were pooled, dried (Na2SO4), filtered and concentrated to give the title compound (5.71 g, quant. yield): 1H NMR (400 MHz, DMSO-d6) delta ppm 3.94 (s, 3H), 7.04 (t, 1 H), 8.10-8.16 (m, 1H), 8.48 (m, 1H); MS (ES+) m/z 238 [M+H]+.
100%	With diethylamino-sulfur trifluoride; In dichloromethane; at 0℃; for 48h;	To a mixture of <strong>[103058-87-3]5-bromo-2-methoxynicotinaldehyde</strong> (10.0 g, 46.3 mmol) in dry DCM (100 mL) under N2 at 0 C. was added DAST (29.8 g, 185.2 mmol) and stirred at 0 C. for 2 days. The reaction was quenched with 100 mL of a saturated NaHCO3 solution. The aqueous layer was extracted with DCM (100 mL*3). The combined organic layers were washed with NaHCO3 (sat, 100 mL) and brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give 5-bromo-3-(difluoromethyl)-2-methoxypyridine as a yellow oil (11.0 g). Yield 100% (ESI 238.1 (M+H)+).

References: [1]Patent: US2012/165346,2012,A1 .Location in patent: Page/Page column 18.
[2]Patent: US2019/315692,2019,A1 .Location in patent: Paragraph 0228; 1120; 1121.

3
[ 1154740-48-3 ]
[ 1254123-51-7 ]
[ 1446002-28-3 ]

Yield	Reaction Conditions	Operation in experiment
18%	With dicyclohexyl-(2?,4?,6?-triisopropyl-3,6-dimethoxy-[1,1?-biphenyl]-2-yl)phosphine; chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2?,4?,6?-tri-1-propyl-1,1?-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); sodium t-butanolate; In 1,4-dioxane; at 100℃; for 66h;	b) 6-Bromo-4-(5-difluoromethyl-6-methoxy-pyridin-3-yl)-5-methyl-3,4-dihydro-2H-benzo[1,4]oxazine A solution of <strong>[1154740-48-3]6-bromo-5-methyl-3,4-dihydro-2H-benzo[1,4]oxazine</strong> (500 mg, 2.19 mmol), Intermediate IA6 (574 mg, 2.41 mmol), NaOtBu (421 mg, 4.38 mmol), BrettPhos (CAS registry 1070663-78-3) (59 mg, 0.11 mmol) and [BrettPhos]palladacycle (CAS registry 1148148-01-9) (88 mg, 0.11 mmol) in dioxane (11 ml) was stirred at 100 C. for 18 h. Catalyst and ligand were reloaded and stirring was continued at 100 C. for 48 h. The reaction mixture was cooled down to rt, diluted with EtOAc and washed with sat. aq. NaHCO3 soln. The organic layer was dried over MgSO4, concentrated to afford a brown oil. Purification by flash chromatography on silica gel (cyclohexane/EtOAc 100:0 to 80:20) afforded the title compound as a brown oil (150 mg, 18% yield). HPLC RtM1=1.34 min; ESIMS: 385, 387 [(M+H)+].

References: [1]Patent: US2013/165436,2013,A1 .Location in patent: Paragraph 0687; 0688.

4
[ 1254123-51-7 ]
[ 73183-34-3 ]
[ 1445651-49-9 ]

Yield	Reaction Conditions	Operation in experiment
33%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 80℃; for 18.0h;Inert atmosphere;	Bis-(pinacolato)-diborane (CAS registry 73183-34-3) (160 mg, 0.63 mmol), KOAc (CAS registry 127-08-2) (165 mg, 1 .68 mml) and PdCI2(dppf)-CH2CI2 adduct (CAS registry 72287- 26-4) (34 mg, 0.04 mmol), were placed in a vial which was degassed and backfilled with N2.A solution of 5-bromo-3-difluoromethyl-2-methoxy-pyridine (CAS registry 1254123-51 -7) (100 mg, 0.42 mmol) in dioxane (2.8 ml) was added and the reaction mixture was heated at 80C for 18 h. The mixture was cooled down and EtOAc (3 ml) was added and the mixture was filtered through hyflo. The dark filtrate was concentrated (245 mg as a brown oil) and then diltuted with heptane (3 ml). The dark solid was filtered off and the filtrate was evaporated and purified by flash chromatography on silica gel (cyclohexane / EtOAc 100:00 to 85:15) to afford the title compound as a colorless oil (40 mg, 33% yield). HPLC RtMO1 =1.28 min; ESIMS: 286 [(M+H)+].

References: [1]Patent: WO2013/93850,2013,A1 .Location in patent: Page/Page column 89.

5
[ 1254123-51-7 ]
1-((R)-3-{(S)-3-[4-(5-difluoromethyl-6-methoxypyridin-3-yl)-5-methylquinolin-6-yloxy]pyrrolidine-1-carbonyl}pyrrolidin-1-yl)ethanone [ No CAS ]

References: [1]Patent: WO2013/93850,2013,A1 .

6
[ 1254123-51-7 ]
[ 1445651-25-1 ]

References: [1]Patent: WO2013/93850,2013,A1 .

7
[ 1254123-51-7 ]
[ 1445651-42-2 ]

References: [1]Patent: WO2013/93850,2013,A1 .

8
[ 1254123-51-7 ]
[ 1445651-43-3 ]

References: [1]Patent: WO2013/93850,2013,A1 .

9
[ 1254123-51-7 ]
[ 1445651-26-2 ]

References: [1]Patent: WO2013/93850,2013,A1 .

10
[ 1254123-51-7 ]
5-bromo-3-(difluoromethyl)pyridin-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73.2%	With hydrogen bromide; acetic acid; at 20 - 40℃; for 6.25h;	A mixture of <strong>[1254123-51-7]5-bromo-3-(difluoromethyl)-2-methoxypyridine</strong> (11.0 g, 46.2 mmol) in HBr (33% in acetic acid, 100 mL) was stirred at room temperature for 5 hours and then at 40 C. for 75 mins. The mixture was concentrated and poured into 100 mL of saturated NaHCO3 solution and extracted with DCM. The combined organic layers dried over Na2SO4 and concentrated in vacuo to give 5-bromo-3-(difluoromethyl)pyridin-2-ol as a white solid (8.5 g) used without further purification. Yield 73.2% (ESI 226.0 (M+H)+).
73.2%	With hydrogen bromide; acetic acid; at 40℃; for 6.25h;	A mixture of <strong>[1254123-51-7]5-bromo-3-(difluoromethyl)-2-methoxypyridine</strong> (11.0 g, 46.2 mmol) in HBr (33% in acetic acid, 100 mL) was stirred at room temperature for 5 hours and then at 40oC for 75 mins. The mixture was concentrated and poured into 100 mL of saturated NaHCO3solution and extracted with DCM. The combined organic layers dried over Na2SO4 and concentrated in vacuo to give 5-bromo-3-(difluoromethyl)pyridin-2-ol as a white solid (8.5 g) used without further purification. Yield 73.2% (ESI 226.0(M+H)+).

References: [1]Patent: US2019/315692,2019,A1 .Location in patent: Paragraph 0228; 1122; 1123.
[2]Patent: WO2021/76890,2021,A1 .Location in patent: Page/Page column 239; 288.

11
[ 1254123-51-7 ]
ethyl 2-(5-bromo-3-(difluoromethyl)-2-oxopyridin-1(2H)-yl)-4-methylpentanoate [ No CAS ]