[ CAS No. 742100-75-0 ] {[proInfo.proName]}

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Quality Control of [ 742100-75-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 742100-75-0 ]

Product Details of [ 742100-75-0 ]

CAS No. :	742100-75-0	MDL No. :	MFCD08688594
Formula :	C₆H₅BrClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZZGSPGXWLOYKFH-UHFFFAOYSA-N
M.W :	222.47	Pubchem ID :	23091039
Synonyms :

Safety of [ 742100-75-0 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338+P310-P332+P313-P362-P403+P233-P405-P501	UN#:	3261
Hazard Statements:	H302-H315-H318-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 742100-75-0 ]

* 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 [ 742100-75-0 ]
Downstream synthetic route of [ 742100-75-0 ]

[ 742100-75-0 ] Synthesis Path-Upstream 1~1

1
[ 742100-75-0 ]
[ 228251-24-9 ]

Reference： [1] Patent: WO2009/10801, 2009, A1, . Location in patent: Page/Page column 72
[2] Patent: EP1593673, 2005, A1, . Location in patent: Page/Page column 98
[3] Patent: WO2011/103202, 2011, A2, . Location in patent: Page/Page column 180
[4] Patent: WO2015/181747, 2015, A1, . Location in patent: Page/Page column 76
[5] Patent: WO2017/133701, 2017, A1, . Location in patent: Paragraph 157; 158

[ 742100-75-0 ] Synthesis Path-Downstream 1~4

1
[ 104612-36-4 ]
[ 742100-75-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2566 - 2569

2
[ 78686-79-0 ]
[ 742100-75-0 ]

Yield	Reaction Conditions	Operation in experiment
		Reference Example 153 To a suspension of calcium chloride (33.6 g) in ethanol (250 ml) and tetrahydrofuran (250 ml) was added sodium borohydride (23.0 g) at 0C portionwise. After stirring for 1 hour at 0C with a calcium chloride tube equipped, <strong>[78686-79-0]methyl 5-bromo-2-chloronicotinate</strong> (19.0 g) was added thereto, and the mixture was stirred as such overnight at 0C. The reaction mixture was acidified with 2.5 N hydrochloric acid at 0C, which was returned to room temperature and stirred for 1 hour. After neutralization with an aqueous sodium hydrogen carbonate solution, the insolubles were removed by filtration. The solvent was distilled off under reduced pressure, and then the resulting residue was purified by silica gel column chromatography (hexane: ethyl acetate = 9: 1 ? hexane: ethyl acetate = 4: 1) to give (5-bromo-2-chloropyridin-3-yl)methanol (15.0 g) as colorless crystals. m.p. 86.7-87.5C. 1R-NMR (300 MHz, CDCl3) delta 4.77 (2H, s), 8.04 (1H, d, J=2.4 Hz), 8.36 (1H, d, J=2.4 Hz). Elementary analysis C6H5NOClBr, Calcd. C, 32.39; H, 2.27; N, 6.30: Found C, 32.38; H, 2.24; N, 6.28.
		To a mixture of NaBH4 (5.8 g, 152. 6 mmol, 4 eq) and anhydrous CaCl2 (16.9 g, 152. 6 mmol) in dry DCM (100 mL) at 0C, was added slowly <strong>[78686-79-0]methyl 5-bromo-2-chloronicotinate</strong> (9.5 g, 38.15 mmol). The resulting mixture was stirred at room temperature for 12h. Water was added to the reaction mixture at 0C. The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo, to afford 6.8 g (crude) of (5-bromo-2-chloropyridin-3- yl)methanol, which was used in the next step without further purification. LCMS [M+H]+ 223.1.
	With sodium tetrahydroborate; calcium chloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; at 0 - 90℃;Inert atmosphere;	To methy? 5-bromo-2-choronicotinate (5.92 g, 23.6 mmo) in DCM (70 mD under N2 atmosphere at RT were added anhydrous CaC2 (10.5 g, 94 mmo) then at 0C porfionwise NaBH (3.57 g, 94 mmo). The reaction mixture was stirred at RT overnight. THF (70.0 mD was added and the mixture was stirred at 60C for 24h. I ,4-dioxane (70 mD was added and the mixture was stirred at 90C for 28h After coo?ing to 0C, the reaction mixture was quenched carefuHy with water and stirred at RT overnight. Lithium sa?ts were coHected by fi[tration through a pad of ceHte and washed with THF. The fi?trate was dHuted with water and AcOEt, the organic phase was separated and the aqueous phase was extracted with AcOEt. The combined organic phases were washed with brine, dried over Na2SO4, fitered and evaporated to dryness to afford (5-bromo-2- choropyridin-3-y)methanoL M/z = 222/224/226 [M+Hj+, Rt = 0.70 mm (UPLC Method B2). 1H NMR (400MHz, DM80 d6) O ppm: 8,47 (m, IH), 8.08-8.07 (m, IH). 5.69 (t, IH), 4.53 (d, 2H)

Reference： [1]Patent: EP1593673,2005,A1 .Location in patent: Page/Page column 98
[2]Patent: WO2011/103202,2011,A2 .Location in patent: Page/Page column 180
[3]Patent: WO2015/181747,2015,A1 .Location in patent: Page/Page column 76

3
[ 742100-75-0 ]
[ 228251-24-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridinium chlorochromate; In dichloromethane; at 18 - 25℃; for 2h;	(5-Bromo-2-chloropyridin-3-yl)methanol (Intermediate 3, 0.67 g, 3.01 mmol) and pyridinium chlorochromate (0.779 g, 3.61 mmol) were combined in anhydrous dichloromethane (10 ml) and stirred at room temperature. The reaction was stirred for 2 hours. The reaction mixture was diluted with diethyl ether and filtered. The filtrate was concentrated to a tan solid. The solid was suspended in methanol and deposited onto Isolute and dried. Purification by normal phase Isco column (40%- 100% dichloromethane/hexane) afforded the desired compound as a white solid(0.24g).MS (ES) MH+: 220 for C6H3BrClNO.1H NMR: 8.40 (s, IH), 8.85 (s, IH), 10.18 (s, IH)
		Reference Example 154 To a solution of oxalyl chloride (1.98 ml) in dichloromethane (20 ml) was added dropwise a solution of DMSO (3.45 ml) in dichloromethane (30 ml) at -78C under a nitrogen atmosphere. The mixture was stirred as such for 10 minutes, and then a solution of 5-bromo-2-chloropyridin-3-yl)methanol (3.6 g) in dichloromethane (35 ml) was added dropwise thereto. The mixture was stirred as such for 10 minutes, and then triethylamine (13.5 ml) was added dropwise thereto. After stirring as such for 10 minutes, the resulting mixture was returned to room temperature and stirred for 1 hour. To the reaction solution was added water, followed by separation. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the resulting residue was purified by silica gel column chromatography (hexane: ethyl acetate = 6: 1) to give 5-bromo-2-chloronicotinaldehyde (3.4 g) as colorless crystals. m.p. 88.0-89.0C. 1H-NMR (300 MHz, CDCl3) delta 8.33 (1H, d, J=2.7 Hz), 8.67 (1H, d, J=2.7 Hz), 10.38 (1H, s). Elementary analysis C6H3NOClBr, Calcd. C, 32.69; H, 1.37; N, 6.35: Found C, 32.51; H, 1.33; N, 6.18.
	With Dess-Martin periodane; In dichloromethane; at 0 - 20℃; for 12h;	To a solution of (5-bromo-2-chloropyridin-3-yl)methanol (6.8 g, 30.6 mmol) in DCM (200 mL), was added Dess-Martin periodinane (32.4 g, 76.6 mmol) at 0C. The resulting mixture was stirred at room temperature for 12h. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (0 to 30% EtOAc in petroleum ether) to afford 5.05 g of 5-bromo-2-chloronicotinaldehyde. LCMS [M+H]+ 221.1.

	With manganese(IV) oxide; In dichloromethane; at 20℃; for 9h;Inert atmosphere;	To (5-bromo-2-choropyridin-3-y)methano (5.24 g, 22.1 mmo) in DCM (250 m) under N2 atmosphere was added Mn02 (19.2 g, 22.1 mmo). After 2h of stirring at RT, Mn02 (3.85 g, 44.2 mmo) was added, the reaction mixture was stirred for 3h at RT. Then Mn02 (1.92 g, 22.1 mmo) was added and the mixture was stirred at RT for 4h. Mn02 was coHected by fi?tration through a pad of cehte, washed with DCM and the fitrate was evaporated. The residue was purified by flash co?umn chromatography on siHca g& (hexane/TBME 1/0 to 3/7) to afford 5-bromo-2-choronicotinadehyde. Rt = 1.02 mm (UPLC Method B2), 1H NMR (400 MHz, DMSO-d5) O ppm: 10.19 (s, IH), 8.85 (d, IH), 8.39(d, IH).
		To a solution of(COC1)2 (2.95 mL, 34.84 mmol) in dried DCM (26 mL) at -78 C was added a solution of DMSO (4.94 mL, 69.7mmol) in DCM (45 mL) dropwise, and stirred at-78C for 10 mm. Then a solution of (5-bromo-2-chloropyridin-3-yl)methanol (B-2) in DCM (45 mL) was added dropwise. The mixture was stirred at -78C for 10 mm. TEA (18.2 mL, 131 mmol) was added dropwise, and stirred for 1 h at -78C. The mixture was warmed to r.t. and stirred for 1 h. The mixture was diluted with water (100 mL). Layers were separated. The organic layer was washed with water and brine, dried over MgSO4, and concentrated. The residue was purified by column chromatography on silica gel eluting with 3-5% EA in hexane to give 5-bromo-2-chloronicotinaldehyde (B-3) as a white solid. MS-ESI (m/z): 220 [M + 1]

Reference： [1]Patent: WO2009/10801,2009,A1 .Location in patent: Page/Page column 72
[2]Patent: EP1593673,2005,A1 .Location in patent: Page/Page column 98
[3]Patent: WO2011/103202,2011,A2 .Location in patent: Page/Page column 180
[4]Patent: WO2015/181747,2015,A1 .Location in patent: Page/Page column 76
[5]Patent: WO2017/133701,2017,A1 .Location in patent: Paragraph 157; 158

4
[ 742100-75-0 ]
[ 1332392-76-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: manganese(IV) oxide / dichloromethane / 9 h / 20 °C / Inert atmosphere 2: diethylamino-sulfur trifluoride / ethanol; dichloromethane / 2 h / 20 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: Dess-Martin periodane / dichloromethane / 12 h / 0 - 20 °C 2: diethylamino-sulfur trifluoride / ethanol / dichloromethane / 2 h / 20 °C
	Multi-step reaction with 2 steps 1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C 2: diethylamino-sulfur trifluoride / dichloromethane / 1 h / 0 - 15 °C

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2015/181747, 2015, A1
[2]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2011/103202, 2011, A2
[3]Current Patent Assignee: OGAWA ANTHONY KEN; LANG SIMON B; CHENG ALAN C; HICKS JACQUELINE D; SHEARN NANCE GALEN PAUL; HAYES DONNA A A W; TAOKA BRANDON M; LOMBARDO MATTHEW J; SINZ CHRISTOPHER J; MERCK & CO INC - WO2021/257353, 2021, A1

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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 742100-75-0 ] {[proInfo.proName]}

Quality Control of [ 742100-75-0 ]

Related Doc. of [ 742100-75-0 ]

Product Details of [ 742100-75-0 ]

Safety of [ 742100-75-0 ]

Application In Synthesis of [ 742100-75-0 ]

[ 742100-75-0 ] Synthesis Path-Upstream 1~1

[ 742100-75-0 ] Synthesis Path-Downstream 1~4

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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