1206968-77-5|2-(5-Bromopyridin-2-yl)ethanol| Ambeed

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Quality Control of [ 1206968-77-5 ] Purity: 98% SDS Specification

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Product Details of [ 1206968-77-5 ]

CAS No. :	1206968-77-5
Formula :	C₇H₈BrNO
M.W :	202.05
SMILES Code :	BrC1=CN=C(CCO)C=C1
MDL No. :	MFCD09999981
InChI Key :	RXFPLSUXRPOSOF-UHFFFAOYSA-N
Pubchem ID :	53403688

Safety of [ 1206968-77-5 ]

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

Application In Synthesis of [ 1206968-77-5 ]

* 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.

Downstream synthetic route of [ 1206968-77-5 ]

[ 1206968-77-5 ] Synthesis Path-Downstream 1~35

1
[ 1206968-77-5 ]
[ 18162-48-6 ]
[ 691900-89-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 1H-imidazole; In dichloromethane; at 0℃; for 1h;	Step A: To a solution of 2, 5-dibromopyridine (2.4g) in toluene was added tributylallyltin (3.4 ML) and dichlorobis (TRIPHENYLPHOSPHINE) palladium (0.7g) under nitrogen atmosphere. The mixture was refluxed for a couple of hours and concentrated under reduced pressure. The residue was re-dissolved in "wet ether"and added DBU (3ml) slowly to give a cloudy solution. The mixture was filtered over a pad of silica gel and concentrated. The residue was dissolved in methylene CHLORIDE/METHANOL=L/L solution and cooled to-78 C. To this solution was bubbled though ozone until the reaction mixture became a blue color. The reaction was warmed to 0 C and added sodium borohydride (0. 5G) portion-wise. After stirring at 0 C for 1 hour, the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with 1N NAOHAQ, brine, dried (MGSO4), and concentrated under reduced pressure to afford crude alcohol. The alcohol was purified by silica gel (methylene CHLORIDE/ETHYL ACETATE=1/1) to give desired alcohol. To a solution of alcohol in methylene chloride was added imidazole (0.4g) and TBS-C1 (0.8g) at 0 C. The mixture was stirred for 1 hour. The reaction was poured into 0.1 N HCLAQ extracted with methylene chloride. The organic layer was washed with brine, dried (MgSO4) and evaporated. The residue was purified by silica gel (100% methylene chloride) to give desired compound (1. 05G). H NMR (CDCL3) : 8 8.61 (1H, d); 7.73 (1H, dd); 7.14 (1H, d); 3.97 (2H, t); 2. 96 (2H, t); 0.86 (9H, s);- 0.02 (6H, s).
	With 1H-imidazole; In dichloromethane; at 0℃; for 1h;	Example 10 1-(3-{ [6-(2 HYDROXYETHYL) PYRIDINE-3-YL] CARBONYL}-6-METHOXY-LH-INDAZOL-1-YL)-3, 3-dimethylbutan-2-one Step A: To a solution of 2,5-dibromopyridine (2.4g) in toluene was added tributylallyltin (3.4 ml) and dichlorobis (triphenylphosphine) palladium (0.7g) under nitrogen atmosphere. The mixture was refluxed for a couple of hours and concentrated under reduced pressure. The residue was re-dissolved in"wet ether"and added DBU (3ml) slowly to give a cloudy solution. The mixture was filtered over a pad of silica gel and concentrated. The residue was dissolved in methylene chloride/methanol=l/l solution and cooled TO-78 C. To this solution was bubbled though ozone until the reaction mixture became a blue color. The reaction was warmed to 0 C and added sodium borohydride (0. 5G) portion-wise. After stirring at 0 C for 1 hour, the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with IN NaOHaq, brine, dried (MGSO4), and concentrated under reduced pressure to afford crude alcohol. The alcohol was purified by silica gel (methylene chloride/ethyl ACETATE=1/1) to give desired alcohol. To a solution of alcohol in methylene chloride was added imidazole (0.4g) and TUBS-CL (0.8g) at 0 C. The mixture was stirred for 1 hour. The reaction was poured into 0.1 N HCLAQ extracted with methylene chloride. The organic layer was washed with brine, dried (MGS04) and evaporated. The residue was purified by silica gel (100% methylene chloride) to give desired compound. H NMR (CDC13) : 8 8. 61 (1H, d); 7.73 (1H, dd); 7.14 (1H, d); 3.97 (2H, t); 2.96 (2H, t); 0.86 (9H, s);- 0.02 (6H, s).
	With 1H-imidazole; In dichloromethane; at 0℃; for 1h;	[0196] To a solution of 2,5-dibromopyridine (2.4 g) in toluene was added tributylallyltin (3.4 ml) and dichlorobis(triphenylphosphine) palladium (0.7 g) under nitrogen atmosphere. The mixture was refluxed for a couple of hours and concentrated under reduced pressure. The residue was re-dissolved in “wet ether” and added DBU (3 ml) slowly to give a cloudy solution. The mixture was filtered over a pad of silica gel and concentrated. The residue was dissolved in methylene chloride/methanol=1/1 solution and cooled to -78 C. To this solution was bubbled though ozone until the reaction mixture became a blue color. The reaction was warmed to 0 C. and added sodium borohydride (0.5 g) portion-wise. After stirring at 0 C. for 1 hour, the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with 1N NaOHaq, brine, dried (MgSO4), and concentrated under reduced pressure to afford crude alcohol. The alcohol was purified by silica gel (methylene chloride/ethyl acetate=1/1) to give desired alcohol. To a solution of alcohol in methylene chloride was added imidazole (0.4 g) and TBS-Cl (0.8 g) at 0 C. The mixture was stirred for 1 hour. The reaction was poured into 0.1 N HClaq extracted with methylene chloride. The organic layer was washed with brine, dried (MgSO4) and evaporated. The residue was purified by silica gel (100% methylene chloride) to give desired compound. [0197] 1H NMR (CDCl3): δ 8.61 (1H, d); 7.73 (1H, dd); 7.14 (1H, d); 3.97 (2H, t); 2.96 (2H, t); 0.86 (9H, s); -0.02 (6H, s).

References: [1]Patent: WO2005/25568,2005,A1 .Location in patent: Page/Page column 24.
[2]Patent: WO2005/26128,2005,A1 .Location in patent: Page/Page column 36-37.
[3]Patent: US2004/97575,2004,A1 .Location in patent: Page 18.

2
C₈H₈BrN [ No CAS ]
[ 1206968-77-5 ]

Yield	Reaction Conditions	Operation in experiment
		Step A: To a solution of 2, 5-dibromopyridine (2.4g) in toluene was added tributylallyltin (3.4 ML) and dichlorobis (TRIPHENYLPHOSPHINE) palladium (0.7g) under nitrogen atmosphere. The mixture was refluxed for a couple of hours and concentrated under reduced pressure. The residue was re-dissolved in "wet ether"and added DBU (3ml) slowly to give a cloudy solution. The mixture was filtered over a pad of silica gel and concentrated. The residue was dissolved in methylene CHLORIDE/METHANOL=L/L solution and cooled to-78 C. To this solution was bubbled though ozone until the reaction mixture became a blue color. The reaction was warmed to 0 C and added sodium borohydride (0. 5G) portion-wise. After stirring at 0 C for 1 hour, the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with 1N NAOHAQ, brine, dried (MGSO4), and concentrated under reduced pressure to afford crude alcohol. The alcohol was purified by silica gel (methylene CHLORIDE/ETHYL ACETATE=1/1) to give desired alcohol. To a solution of alcohol in methylene chloride was added imidazole (0.4g) and TBS-C1 (0.8g) at 0 C. The mixture was stirred for 1 hour. The reaction was poured into 0.1 N HCLAQ extracted with methylene chloride. The organic layer was washed with brine, dried (MgSO4) and evaporated. The residue was purified by silica gel (100% methylene chloride) to give desired compound (1. 05G). H NMR (CDCL3) : 8 8.61 (1H, d); 7.73 (1H, dd); 7.14 (1H, d); 3.97 (2H, t); 2. 96 (2H, t); 0.86 (9H, s);- 0.02 (6H, s).
		[0196] To a solution of 2,5-dibromopyridine (2.4 g) in toluene was added tributylallyltin (3.4 ml) and dichlorobis(triphenylphosphine) palladium (0.7 g) under nitrogen atmosphere. The mixture was refluxed for a couple of hours and concentrated under reduced pressure. The residue was re-dissolved in “wet ether” and added DBU (3 ml) slowly to give a cloudy solution. The mixture was filtered over a pad of silica gel and concentrated. The residue was dissolved in methylene chloride/methanol=1/1 solution and cooled to -78 C. To this solution was bubbled though ozone until the reaction mixture became a blue color. The reaction was warmed to 0 C. and added sodium borohydride (0.5 g) portion-wise. After stirring at 0 C. for 1 hour, the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with 1N NaOHaq, brine, dried (MgSO4), and concentrated under reduced pressure to afford crude alcohol. The alcohol was purified by silica gel (methylene chloride/ethyl acetate=1/1) to give desired alcohol. To a solution of alcohol in methylene chloride was added imidazole (0.4 g) and TBS-Cl (0.8 g) at 0 C. The mixture was stirred for 1 hour. The reaction was poured into 0.1 N HClaq extracted with methylene chloride. The organic layer was washed with brine, dried (MgSO4) and evaporated. The residue was purified by silica gel (100% methylene chloride) to give desired compound. [0197] 1H NMR (CDCl3): δ 8.61 (1H, d); 7.73 (1H, dd); 7.14 (1H, d); 3.97 (2H, t); 2.96 (2H, t); 0.86 (9H, s); -0.02 (6H, s).

References: [1]Patent: WO2005/25568,2005,A1 .Location in patent: Page/Page column 24.
[2]Patent: US2004/97575,2004,A1 .Location in patent: Page 18.

3
[ 624-28-2 ]
[ 24850-33-7 ]
[ 1206968-77-5 ]

Yield	Reaction Conditions	Operation in experiment
		Example 10 1-(3-{ [6-(2 HYDROXYETHYL) PYRIDINE-3-YL] CARBONYL}-6-METHOXY-LH-INDAZOL-1-YL)-3, 3-dimethylbutan-2-one Step A: To a solution of 2,5-dibromopyridine (2.4g) in toluene was added tributylallyltin (3.4 ml) and dichlorobis (triphenylphosphine) palladium (0.7g) under nitrogen atmosphere. The mixture was refluxed for a couple of hours and concentrated under reduced pressure. The residue was re-dissolved in"wet ether"and added DBU (3ml) slowly to give a cloudy solution. The mixture was filtered over a pad of silica gel and concentrated. The residue was dissolved in methylene chloride/methanol=l/l solution and cooled TO-78 C. To this solution was bubbled though ozone until the reaction mixture became a blue color. The reaction was warmed to 0 C and added sodium borohydride (0. 5G) portion-wise. After stirring at 0 C for 1 hour, the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with IN NaOHaq, brine, dried (MGSO4), and concentrated under reduced pressure to afford crude alcohol. The alcohol was purified by silica gel (methylene chloride/ethyl ACETATE=1/1) to give desired alcohol. To a solution of alcohol in methylene chloride was added imidazole (0.4g) and TUBS-CL (0.8g) at 0 C. The mixture was stirred for 1 hour. The reaction was poured into 0.1 N HCLAQ extracted with methylene chloride. The organic layer was washed with brine, dried (MGS04) and evaporated. The residue was purified by silica gel (100% methylene chloride) to give desired compound. H NMR (CDC13) : 8 8. 61 (1H, d); 7.73 (1H, dd); 7.14 (1H, d); 3.97 (2H, t); 2.96 (2H, t); 0.86 (9H, s);- 0.02 (6H, s).

References: [1]Patent: WO2005/26128,2005,A1 .Location in patent: Page/Page column 36-37.

4
[ 192642-85-6 ]
[ 1206968-77-5 ]

Yield	Reaction Conditions	Operation in experiment
80%		[Example 60]tert-Butyl 4-[2-[2-(4-methanesulfonylphenoxyethyl)pyridine-5-yl]piperidine-1-carboxylate (1) 2-(5-Bromopyridin-2-yl)ethanol To a solution of (5-bromopyridin-2-yl)acetic acid (60.0 mg, 0.278 mmol) in dry tetrahydrofuran (1.4 mL) was added dropwise borane- tetrahydrofuran complex (1.06M in tetrahydrofuran, 0.34 mL, 0.361 mmol) under N2. The mixture was stirred at room temperature for 19 hours and water(5 mL)-acetic acid (5 mL) was added slowly. The mixture was concentrated under reduced pressure, the residue was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/1→ethyl acetate) to give the title compound as a yellow oil (45 mg, yield 80%).1H NMR(CDCl3,400 MHz): δ= 2.98(2H, t, J=5 Hz), 3.68(1H, brs), 4.01(2H, t, J=5 Hz), 7.09(1H, d, J=8 Hz), 7.75(1H, dd, J=2 Hz, 8 Hz), 8.57(1H, d, J=2 Hz).
79%	With diborane; In tetrahydrofuran; at -78 - 20℃; for 16h;Inert atmosphere;	[00543] To a solution of Example 105a (2.16 g, 10.0 mmol) in dry THF (80 mL) was added slowly added BH3/THF (1.0 M, 30 mL) at -78C under nitrogen atmosphere. After addition, the mixture was allowed to stir from -78C to r.t. for 16 h. The reaction was quenched by saturated aqueous K2C03, extracted by EtOAc (50 mL*2), dried over Na2S04, filtered and concentrated. The residue was purified by silica gel chromatography (Petroleum Ether/EtOAc = 30/70) to give the desired product Example 105b (1.6 g, yield 79%) as colorless oil. LCMS [M+l]+ =202.0/204.0
51%	With borane-THF; In tetrahydrofuran; at 20℃; for 4h;Inert atmosphere;	To a stirred solution of 2-(5-bromopyridin-2-yl)acetic acid (2 g, 9.25 mmol) in THF (50 mL) was added BH3.THF (12 mL, 12.03 mmol, 1M in THF) drop wise at room temperature under nitrogen and stirred at same temperature for 24 h. The mixture was cooled to 0 C, quenched with water: acetic acid (10 mL, 1:1) and stirred at room temperature for 30 minutes. The reaction mixture was evaporated and resulting residue was diluted with EtOAc (50 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution and water, dried, filtered and evaporated. The crude compound was chromatographed on silica eluting with 40% EtOAc in petroleum ether affording a yellow liquid (950 mg, 51%). M/z = 202.0 (M+H)+.

		Preparation of 6:2-(5-Bromopyridin-2-yl)ethanolUnder N2, a solution of 2-(5-bromopyridin-2-yl)acetic acid (5, 29.75 g) in THF (450 mL) was cooled to 0C. Borane THF complex (1 M in THF, 413.2 mL, 413.2 mmol) was added dropwise, keeping the reaction temperature below 5C. The mixture was allowed to warm to room temperature and stir for 4h. The mixture was cooled to 0C and saturated aqueous K2C03 solution (500 mL) and H20 (500 mL) were added slowly. The mixture was extracted with EtOAc (3x 500 mL). The combined organic layers were washed with brine (500 mL), dried over Na2S04 and filtered. The solvent was removed in vacuo and the residue was purified by column chromatography (silica,Heptane/EtOAc 3:7) yielding compound 6 (10.9 g, 53.9 mmol, 40% over 2 steps). 1 H- NMR (CDCI3, 300 MHz): δ 3.00 (t, 2H, CH2), 3.64 (bs, 1 H, OH), 4.03 (t, 2H, CH2), 7.10 (d, 1 H, ArH), 7.76 (dd, 1 H, ArH), 8.59 (d, 1 H, ArH).
1.09 g	With borane-THF; In tetrahydrofuran; at 5 - 20℃;	Commercially available 2-(5-bromopyridin-2-yl)acetic acid (1.00 g, 4.6 mmol) in tetrahydrofuran (10 mL) is cooled to 5 C. and treated dropwise over 10 minutes with borane-tetrahydrofuran complex (13.9 mL, 13.9 mmol). After stirring at room temperature for 4 hours, the reaction mixture is quenched with saturated aqueous potassium carbonate (20 mL), extracted with ethyl acetate (50 mL), dried over MgSO4, filtered, the solvent removed under reduced pressure, and the crude material purified by column chromatography on silica gel eluting with a gradient of neat heptane to neat ethyl acetate to afford the title compound (1.09 g): m/z (CI) 203 [M+H].

References: [1]Patent: EP2311822,2011,A1 .Location in patent: Page/Page column 51.
[2]Patent: WO2019/51265,2019,A1 .Location in patent: Paragraph 00543.
[3]Patent: EP3628672,2020,A1 .Location in patent: Paragraph 0506-0508.
[4]Patent: WO2011/45703,2011,A2 .Location in patent: Page/Page column 34.
[5]Patent: US2014/88046,2014,A1 .Location in patent: Paragraph 0111-0112.

5
[ 2402-97-3 ]
[ 1206968-77-5 ]

References: [1]Patent: WO2011/45703,2011,A2 .

6
[ 626-55-1 ]
[ 1206968-77-5 ]

References: [1]Patent: WO2011/45703,2011,A2 .

7
[ 192642-83-4 ]
[ 1206968-77-5 ]

References: [1]Patent: WO2011/45703,2011,A2 .

8
[ 3430-13-5 ]
[ 33513-42-7 ]
[ 1206968-77-5 ]

Yield	Reaction Conditions	Operation in experiment
87%		A 2.5 M solution of n-butyllithium in pentane (6.97 ml, 17.44 mmol) was added dropwise to a solution of DIPEA (3.29 ml, 23.25 mmol) in THF (50 ml). The mixture was stirred at 0 C for 30 min., cooled down to -78 C and then a solution of 5-bromo- 2-methylpyridine (2.0 g, 11.63 mmol) in THF (50 ml) was added. The mixture was stirred at -78 C for a further 2h. and then DMF (8.5 g, 116.26 mmol) was added dropwise. The mixture was stirred at -78 C for 2 h, at 0 C for 30 min. and finally allowed to warm to RT. MeOH (25 ml) and sodium borohydride (0.439 g, 11.6 mmol) were added and the mixture was stirred at RT for a further 30 min. A saturated solution of ammonium chloride was added and the organic layer was separated. The aqueous layer was extracted with EtOAc and the combined organic extracts were dried(Na2S04), filtered and the solvents evaporated in vacuo to yield intermediate 51 (2.8 g, 87%) as a colourless oil.
87%		Example A51 2-(5-Bromo-pyridin-2-yl)-ethanol A 2.5 M solution of n-butyllithium in pentane (6.97 ml, 17.44 mmol) was added dropwise to a solution of DIPEA (3.29 ml, 23.25 mmol) in THF (50 ml). The mixture was stirred at 0 C. for 30 min., cooled down to -78 C. and then a solution of 5-bromo-2-methylpyridine (2.0 g, 11.63 mmol) in THF (50 ml) was added. The mixture was stirred at -78 C. for a further 2 h. and then DMF (8.5 g, 116.26 mmol) was added dropwise. The mixture was stirred at -78 C. for 2 h, at 0 C. for 30 min. and finally allowed to warm to RT. MeOH (25 ml) and sodium borohydride (0.439 g, 11.6 mmol) were added and the mixture was stirred at RT for a further 30 min. A saturated solution of ammonium chloride was added and the organic layer was separated. The aqueous layer was extracted with EtOAc and the combined organic extracts were dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield intermediate 51 (2.8 g, 87%) as a colourless oil.
35%		A two-necked round-bottommed flask equipped with thermometer was charged with anh. THF (2.0 mL) and cooled to -78 C. Then, LDA (2 M in THF/heptane/ethylbenzene, 1.74 mL, 1.5 eq.) was added dropwise at -78 C. The resulting mixture was stirred for 15 min and then solution of 5-bromo-2-methylpyridine (0.4 g, 1.0 eq.) in anh. THF (4.0 mL) was dropped in slowly at -78 C and the reaction mixture was stirred for 1.5 h at -78 C. Afterwards, DMF (1.8 mL, 10.0 eq.) was added dropwise and stirring was continued for 1 h at -78 C. Subsequently, the mixture was allowed to warm to RT and MeOH (4.5 mL) was added followed by NaBH4 (0.089 g, 1.0 eq.). During NaBH4 addition generation of heat was observed, temperature increased to 30 C. The reaction was continued for 30 min at RT and then quenched with saturated NH4Cl aq. solu- tion. The resulting mixture was extracted with EtOAc (3 x). The combined organic layers were washed with brine, dried over anh. Na2SO4, filtered and concentrated in vacuo. The residue was purified by two consecutive FCC (SiHP; DCM:MeOH) and (SiHP; hexane:EtOAc) to give the product (0.204 g, 35% yield) as a yellowish oil. ESI-MS: 202.0 [M+H]+.

References: [1]Patent: WO2011/110545,2011,A1 .Location in patent: Page/Page column 89-90.
[2]Patent: US2012/329792,2012,A1 .Location in patent: Page/Page column 43.
[3]Patent: WO2021/116446,2021,A1 .Location in patent: Page/Page column 153-154.

9
[ 1206968-77-5 ]
[ 1298032-38-8 ]

Yield	Reaction Conditions	Operation in experiment
41%	With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20℃; for 16.5h;	Example A52 5-Bromo-2-(2-methoxy-ethyl)-pyridine A 60% dispersion of sodium hydride in mineral oils, (0.43 g, 11.1 mmol) was added portionwise to a stirred solution of intermediate 51 (2.8 g, 10.1 mmol) in THF (50 ml). The mixture was stirred at 0 C. for 30 min. and at RT for 16 h. A saturated solution of ammonium chloride was added and the organic layer was separated. The aqueous layer was extracted with DCM and the combined organic extracts were dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield 52 (0.9 g, 41%) as a colourless oil.

References: [1]Patent: US2012/329792,2012,A1 .Location in patent: Page/Page column 43.

10
[ 1206968-77-5 ]
[ 1298032-42-4 ]

References: [1]Patent: US2012/329792,2012,A1 .
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 978 - 993.

11
[ 1206968-77-5 ]
[ 20277-69-4 ]
[ 1582262-84-7 ]

Yield	Reaction Conditions	Operation in experiment
570 mg		The product of Step 1 of Example 6 (940 mg, 4.65 mmol) in dimethylformamide (5 mL) at 5 C. is treated with triphenylphosphine (1710 mg, 6.5 mmol) and N-bromosuccinimide (1.24 g, 7.0 mmol) then stirred for 1 hour. Sodium methanesulfinate (980 mg, 9.3 mmol) and tetrabutylammonium iodide (175 mg, 0.45 mmol) are added and the mixture heated at 70 C. for 1 hour then cooled to room temperature, diluted with ethyl acetate (25 mL), washed with water (25 mL) and brine (25 mL), dried over MgSO4, filtered, concentrated, and the crude material purified by column chromatography on silica gel eluting with a gradient of ethyl acetate/heptane to afford the title compound (570 mg): m/z (CI) 265 [M+H].

References: [1]Patent: US2014/88046,2014,A1 .Location in patent: Paragraph 0113-0114.

12
[ 1206968-77-5 ]
[ 1582261-92-4 ]

References: [1]Patent: US2014/88046,2014,A1 .

13
[ 67-56-1 ]
[ 1206968-77-5 ]
[ 1298032-38-8 ]