57684-71-6|3-(Chloromethyl)isoxazole| Ambeed

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Quality Control of [ 57684-71-6 ] Purity: 95% SDS Specification

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Product Details of [ 57684-71-6 ]

CAS No. :	57684-71-6
Formula :	C₄H₄ClNO
M.W :	117.53
SMILES Code :	ClCC1=NOC=C1
MDL No. :	MFCD06809646
InChI Key :	MKFCBJOVMMLPRT-UHFFFAOYSA-N
Pubchem ID :	4913025

Safety of [ 57684-71-6 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H314
Precautionary Statements:	P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501
Class:	8
UN#:	3265
Packing Group:	Ⅱ

Application In Synthesis of [ 57684-71-6 ]

* 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 [ 57684-71-6 ]

[ 57684-71-6 ] Synthesis Path-Downstream 1~33

1
[ 57684-71-6 ]
[ 333-20-0 ]
isoxazol-3-yl-methyl thiocyanate [ No CAS ]

References: [1]Zhurnal Obshchei Khimii,1955,vol. 25,p. 1212,1215; engl. Ausg. S. 1159, 1161.

2
[ 57684-71-6 ]
[ 127-08-2 ]
acetic acid isoxazol-3-ylmethyl ester [ No CAS ]

References: [1]Zhurnal Obshchei Khimii,1955,vol. 25,p. 1212,1215; engl. Ausg. S. 1159, 1161.

3
[ 57684-71-6 ]
[ 30381-48-7 ]
[ 99977-03-4 ]

References: [1]Zhurnal Obshchei Khimii,1957,vol. 27,p. 3210,3213; engl. Ausg. S. 3247, 3248.
Zhurnal Obshchei Khimii,1958,vol. 28,p. 2736,2741; engl. Ausg. S. 2762, 2766.

4
[ 57684-71-6 ]
[ 151-50-8 ]
[ 55242-83-6 ]

References: [1]Zhurnal Obshchei Khimii,1955,vol. 25,p. 1212,1215; engl. Ausg. S. 1159, 1161.

5
[ 57684-71-6 ]
[ 109-89-7 ]
diethyl-isoxazol-3-ylmethyl-amine [ No CAS ]

References: [1]Zhurnal Obshchei Khimii,1955,vol. 25,p. 1212,1215; engl. Ausg. S. 1159, 1161.

6
[ 57684-71-6 ]
[ 62-53-3 ]
[ 99071-59-7 ]

References: [1]Zhurnal Obshchei Khimii,1957,vol. 27,p. 3210,3213; engl. Ausg. S. 3247, 3248.
Zhurnal Obshchei Khimii,1958,vol. 28,p. 2736,2741; engl. Ausg. S. 2762, 2766.

7
[ 57684-71-6 ]
[ 105-53-3 ]
[ 855657-45-3 ]

References: [1]Zhurnal Obshchei Khimii,1955,vol. 25,p. 1212,1215; engl. Ausg. S. 1159, 1161.

8
[ 57684-71-6 ]
[ 121-45-9 ]
isoxazol-3-ylmethyl-phosphonic acid dimethyl ester [ No CAS ]

References: [1]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1954,p. 806,809; engl. Ausg. S. 697, 700.

9
[ 57684-71-6 ]
[ 30842-90-1 ]

References: [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 1937,1939; engl. Ausg. S. 1977, 1979.

10
[ 57684-71-6 ]
[ 76632-20-7 ]

References: [1]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1952,p. 87,91; engl. Ausg. S. 97, 101.

11
[ 57684-71-6 ]
3-iodomethyl-isoxazole [ No CAS ]

References: [1]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1952,p. 87,91; engl. Ausg. S. 97, 101.

12
[ 57684-71-6 ]
[ 131052-58-9 ]

References: [1]Zhurnal Obshchei Khimii,1955,vol. 25,p. 1212,1215; engl. Ausg. S. 1159, 1161.

13
[ 15787-79-8 ]
[ 57684-71-6 ]

Yield	Reaction Conditions	Operation in experiment
78.3%	With hydroxylamine sulfate; In ethanol;Reflux;	Add 400 mL of ethanol to three bottles50.0 g of 1,4-dichloro-3-butenone and 31.0 g of hydroxylamine sulfate.The reaction was heated to reflux and the reaction was monitored by thin layer chromatography.The reaction was poured into 500 mL of ice water, extracted with dichloromethane (100 mL x 3) and the organic phases combined.Washed with saturated sodium bicarbonate, saturated brine, dried over anhydrous sodium sulfate,Under vacuum distillation, 33.1 g (78.3%) of 3-chloromethylisoxazole was collected.
26 g	With hydroxylamine hydrochloride; In methanol; for 4h;Reflux;	Using chloroacetyl chloride and acetylene gas as raw materials, anhydrous aluminum trichloride as catalyst,Methylene chloride is reacted as a solvent to obtain 1,4-dichloro-3-buten-2-one;Further, 1,4-dichloro-3-buten-2-one and hydroxylamine hydrochloride are refluxed in a methanol solvent to obtain 3-chloromethylisoxazole.The specific step of synthesizing 1,4-dichloro-3-buten-2-one is 110 g, and the chloroacetyl chloride having a molar mass of 1.06 is slowly added dropwise to 150 g.Mixing a mixture of anhydrous AlCl3 having a molar mass of 1.17 and 300 ml of CH2Cl2Cooling to -5 C,The acetylene gas was introduced for 2 hours, the reaction was slowly poured into ice water, and the organic layer was washed with cold water and dried over anhydrous sodium sulfate.The fraction of 78-83 C / 16 mmHg was collected under reduced pressure to give an oil of 64 g of 2,4-dichloro-2-but-2-one.The specific step of synthesizing 3-chloromethylisoxazole is to take 50 g of 2,4-dichloro-2-buten-2-one having a molar mass of 0.36.200 ml of methanol and 25 g of hydroxylamine hydrochloride having a molar mass of 0.36 were heated under reflux for 4 hours, and methanol was distilled off under reduced pressure.The Na2CO3 solution was made alkaline, extracted with ethyl acetate, washed with water, dried over anhydrous Na2SO4.Distillation under reduced pressure gave 26 g of 3-chloromethylisoxazole as an oil.

References: [1]Patent: CN103880765,2017,B .Location in patent: Paragraph 0021; 0024; 0025; 0036.
[2]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1952,p. 87,91; engl. Ausg. S. 97, 101.
[3]Patent: CN109251180,2019,A .Location in patent: Paragraph 0014.

14
[ 57684-71-6 ]
[ 100-97-0 ]
isoxazol-3-ylmethyl-hexamethylenetetraminium; chloride [ No CAS ]

References: [1]Zhurnal Obshchei Khimii,1955,vol. 25,p. 1212,1215; engl. Ausg. S. 1159, 1161.

15
[ 57684-71-6 ]
[ 603-35-0 ]
<(3-isoxazolyl)methyl>triphenylphosphonium chloride [ No CAS ]

References: [1]Journal of general chemistry of the USSR,1983,vol. 53,p. 1735 - 1736.
Zhurnal Obshchei Khimii,1983,vol. 53,p. 1926 - 1927.

17
[ 57684-71-6 ]
[ 103360-96-9 ]
[ 120102-11-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In ethanol; toluene; acetonitrile;	STR64 A compound of 3-(chloromethyl)-isoxazole (1.2 g) was added dropwise at a temperature of 20 to 30 C. under stirring to a mixture of 7-fluoro-6-(4,5,6,7-tetrahydro-2H-isoindole-1,3-dion-2-yl)-2H-1,4-benzoxazin-3(4H)-one (3.16 g), acetonitrile (50 ml) and potassium carbonate (1.5 g). The reaction mixture was heated under refluxing for 3 hours, cooled to room temperature, and filtered. The filtrate was concentrated under a reduced pressure to dryness. The resultant residue was mixed with toluene (150 ml) to form a suspension, which was then filtered to remove the undissolved materials therefrom. The filtrate was concentrated under a reduced pressure so as to obtain a viscous material, which was thereafter dissolved in a minimum amount of ethanol. The ethanol solution was cooled to precipitate a crystalline product. This product was separated by filtration and dried, so that the aimed compound, i.e. 7-fluoro-4-(isoxazol-3-ylmethyl)-6-(4,5,6,7-tetrahydro-2H-isoindole-1,3-dion-2-yl)-2H-1,4-benzoxazin-3(4H)-one (3.3 g) was obtained. m.p. 206-210 C.

References: [1]Patent: US4902335,1990,A .

Yield	Reaction Conditions	Operation in experiment
		Thionyl chloride (4.2 ml) was added dropwise to a solution of the product so obtained in chloroform (20 ml) and the mixture was stirred at laboratory temperature for 1 hour. The mixture was evaporated and the crude 3-chloromethylisoxazole so obtained was used without further purification.

19
[ 57684-71-6 ]
[ 131052-59-0 ]

Yield	Reaction Conditions	Operation in experiment
	In ISOPROPYLAMIDE;	The crude product was dissolved in dimethylacetamide (10 ml). Sodium carbonate (approx. 3 g) was added portionwise until the acidity of the reaction mixture was neutralised. Sodium azide (1 equivalent) was added and the mixture was stirred at laboratory temperature for 1.8 hours. The mixture was partitioned between ethyl acetate and water. The organic phase was dried (Na2 SO4) and evaporated. The residue was purified by column chromatography on silica gel using a 1:1 v/v mixture of methylene chloride and hexane as eluent. There was thus obtained 3-azidomethylisoxazole (1.15 g). NMR Spectrum: (CD3 SOCD3) 4.6 (s, 2H), 6.65 (d, 1H), 8.95 (d, 1H).

References: [1]Patent: US5089499,1992,A .

20
[ 89102-73-8 ]
[ 57684-71-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; In tetrachloromethane;	(b) 3-Chloromethyl isoxazole A solution of 3-hydroxymethyl isoxazole (4.23 g, 43 mmol) and triphenylphosphine (11.3 g, 42 mmol) in carbon tetrachloride (100 ml) was heated at reflux for 18 h. Solvent was removed under reduced pressure then the residue taken up in ether and filtered. The filtrate was concentrated under reduced pressure and further purified by short path distillation (bp 60 C. at 10 mm) to give the desired chloride (1.41 g, 12 mmol, 28%); deltaH (CDCl3) 4.50 (2H, s, CH2 --Cl), 6.40 (1H, d, J 2 Hz, CH-4), 8.40 (1H, d, J 2 Hz, CH-5).

References: [1]Patent: US4812470,1989,A .

21
[ 57684-71-6 ]
[ 97908-01-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethyl phosphite;	(c) 3-Diethylphosphonomethyl isoxazole 3-Chloromethyl isoxazole (1.41 g, 12 mmol) and triethylphosphite (3.13 ml, 18 mmol) were heated at 140 C. for 1 h. Distillation (short path) yielded the phosphonate (390 mg, 1.78 mmol, 15%); bp 110-120 C. at 0.7 mm Hg; deltaH (CDCl3) 1.30 (6H, t, J 7 Hz, OCH2 CH3), 3.30 (2H, d, JP-H 22 Hz, CH2 --P), 4.10 (4H, m, OCH2 CH3), 6.40 (1H, s, CH-4), 8.35 (1H, s, CH-5).

References: [1]Patent: US4812470,1989,A .

22
[ 57684-71-6 ]
[ 71-23-8 ]
[ 156-57-0 ]
isopropanol ethanol [ No CAS ]
[ 57684-74-9 ]

Yield	Reaction Conditions	Operation in experiment
	water; In hydrogen bromide;	i. A solution of 3-chloromethylisoxazole (5.8 g) and cysteamine hydrochloride (6.25 g) in aqueous hydrobromic acid (48%, 100 ml) was heated under reflux for 6 hours. Concentration in the presence of water and subsequently n-propanol, followed by recrystallisation of the residue from isopropyl alcohol-ethanol afforded 3-[(2-aminoethyl)-thiomethyl]isoxazole hydrobromide, m.p. 131-133. (Found: Br, 33.6; S, 13.7. C6 H10 N2 OS.HBr requires: Br, 33.4; S, 13.4).
	water; In hydrogen bromide;	i. A solution of 3-chloromethylisoxazole (5.8 g) and cysteamine hydrochloride (6.25 g) in agueous hydrobromic acid (48%, 100 m1) was heated under reflux for 6 hours. Concentration in the presence of water and subsequently n-propanol, followed by recrystallisation of the residue from isopropyl alcohol-ethanol afforded 3-[(2-aminoethyl)-thiomethyl]isoxazole hydrobromide, m.p. 131-133.(Found: Br, 33.6; S, 13.7. C6 H10 N2 OS.HBr requires: Br, 33.4: S, 13.4).
	water; In hydrogen bromide;	a. A solution of 3-chloromethylisoxazole (5.8 g.) and cysteamine hydrochloride (6.25 g.) in aqueous hydrobromic acid (48%, 100 ml) was heated under reflux for 6 hours. Concentration in the presence of water and subsequently n-propanol, followed by recrystallisation of the residue from isopropyl alcohol-ethanol afforded 3-[(2-aminoethyl)thiomethyl]isoxazole hydrobromide, m.p. 131-133. (Found: Br, 33.6; S, 13.7. C6 H10 N2 O S. H Br requires: Br, 33.4; S, 13.4).

water; In hydrogen bromide;

a. A solution of 3-chloromethylisoxazole (5.8 g.) and cysteamine hydrochloride (6.25 g.) in aqueous hydrobromic acid (48%, 100 ml.) was heated under reflux for 6 hours. Concentration in the presence of water and subsequently n-propanol, followed by recrystallisation of the residue from isopropyl alcohol-ethanol afforded 3-[(2-aminoethyl)-thiomethyl]isoxazole hydrobromide, m.p. 131-133. (Found: Br, 33.6; S, 13.7. C6 H10 N2 OS.HBr requires: Br, 33.4; S, 13.4).

References: [1]Patent: US4013769,1977,A .
[2]Patent: US4046907,1977,A .
[3]Patent: US3950333,1976,A .
[4]Patent: US3950353,1976,A .

23
[ 57684-71-6 ]
[ 31681-83-1 ]
[ 893776-87-9 ]

References: [1]Russian Chemical Bulletin,2008,vol. 57,p. 682 - 683.

24
[ 57684-71-6 ]
[ 110-70-3 ]
N,N′-bis(isoxazol-3-ylmethyl)-N,N′-dimethylethane-1,2-diamine [ No CAS ]

References: [1]European Journal of Inorganic Chemistry,2013,p. 3846 - 3857.

25
[ 57684-71-6 ]
[ 1523414-36-9 ]
8-chloro-7-fluoro-1-(isoxazol-3-ylmethyl)-2,2-dimethyl-3,4-dihydropyrimido[1,2-a]pyrimidin-6-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 376 - 400.

26
[ 57684-71-6 ]
[ 1523412-59-0 ]
[ 1523404-96-7 ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 376 - 400.

27
[ 57684-71-6 ]
[ 1523412-61-4 ]
[ 1523410-82-3 ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 376 - 400.

28
[ 57684-71-6 ]
2-(3-methyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)-N-(6'-methyl-5'-(trifluoromethyl)-[2,3-bipyridin]-6-yl)acetamide [ No CAS ]
2-(1-(isoxazol-3-ylmethyl)-3-methyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)-N-(6'-methyl-5'-(trifluoromethyl)-[2,3'-bipyridin]-6-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49.2%	With potassium carbonate; In N,N-dimethyl-formamide; at 55℃; for 18h;Inert atmosphere;	2-(3-methyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)-N-(6?-methyl-5?-(trifluoromethyl)-[2,3- bipyridin]-6-yl)acetamide (50 mg, 0.109 mmol) and potassium carbonate (25 mg, 0.327 mmol) were combined in DMF (3 mL) then <strong>[57684-71-6]3-(chloromethyl)isoxazole</strong> (16 mg, 0.120 mmol) was added. The reaction was heated at 55oC for 18 h, cooled to RT then concentrated to a residue which was purified by chromatography eluted with MeOH/DCM (1:99 to 3:97) to give 2-(1-(isoxazol-3- ylmethyl)-3-methyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)-N-(6?-methyl-5?- (trifluoromethyl)-[2,3?-bipyridin]-6-yl)acetamide (29 mg, 49.2% yield) as a white solid.1H NMR (CDCl3) delta: 9.45 (brd s, 1H), 9.14 (s, 1H), 8.48 (s, 1H), 8.23 (s, 1H), 8.07 (brd s, 1H), 7.82-7.73 (m, 2H), 7.53 (d, J = 8 Hz, 1H), 6.40 (s, 1H), 5.35 (s, 2H), 5.17 (s, 2H) 3.61 (s, 3H), 2.77 (s, 3H). LCMS: MH+ 541 and TR = 3.005 min.

References: [1]Patent: WO2016/44792,2016,A1 .Location in patent: Page/Page column 303.

29
[ 57684-71-6 ]
(S)-2-(3-methyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)-N-(6'-(trifluoromethyl)-[2,3'-bipyridin]-6-yl)propanamide [ No CAS ]
(S)-2-(1-(isoxazol-3-ylmethyl)-3-methyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)-N-(6'-(trifluoromethyl)-[2,3'-bipyridin]-6-yl)propanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	To a solution of (S)-2-(3-methyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)-N-(6'- (trifluoromethyl)-[2,3'-bipyridin]-6-yl)propanamide (15 mg, 0.033 mmol) and POTASSIUM CARBONATE(9 mg, 0.065 mmol) in DMF (1 mL) was added <strong>[57684-71-6]3-(chloromethyl)isoxazole</strong> (3.7 mg, 0.049 mmol). The mixture was stirred at rt overnight. The mixture was diluted with EA and washed with water, saturated aqueous NH4Cl solution and brine, dried over Na2SO4, and evaporated. The residue was purified by silica gel column chromatography (0-2% MeOH/DCM) to give the product (S)-2-(1-(isoxazol-3-ylmethyl)-3-methyl-2,6-dioxo-2,3-dihydro-1H-purin- 7(6H)-yl)-N-(6'-(trifluoromethyl)-[2,3'-bipyridin]-6-yl)propanamide (16.5 mg, 92% yield) as a white solid.1H NMR (400 MHz, DMSO-D6) delta 11.20 (s, 1H), 9.43 (s, 1H), 8.78 (s, 1H), 8.68 (d, J = 1.8 Hz, 1H), 8.39 (s, 1H), 7.89-8.05 (m, 4H), 6.45 (s, 1H), 5.82 (m, 1H), 5.09 (s, 2H), 3.47(s, 3H), 1.87 (d, J = 7.3 Hz, 3H). MH+ 541.

References: [1]Patent: WO2016/44792,2016,A1 .Location in patent: Page/Page column 243; 244.

30
[ 57684-71-6 ]
[ 179557-01-8 ]
tert-butyl 4-[cyclopropyl(1,2-oxazol-3-ylmethyl)amino]piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%		Intermediate 11, tert-butyl 4-(cyclopropylamino)piperid me-i -carboxylate (200 mg, 0.83 mmol) was dissolved in ethanol (10 mL) and sodium bicarbonate (200 mg, 2.38 mmol) was added. The reaction mixture was stirred at 0 C for 30 mm, then Intermediate 14, 3-(chloromethyl)-1 2- oxazole (97 mg, 0.83 mmol) was added dropwise at it The resulting reaction mixture wasstirred at 60 C for 16 h. The solvents were removed in vacuo and the residue was partitioned between H20 (120 mL) and EtOAc (100 mL). The aqueous layer was further extracted with EtOAc (2 x 100 mL) and the combined organic layers were dried (Na2SO4), and the solvents were removed in vacuo. The residue was purified by column chromatography (normal basic activated alumina, 0.5 % to 1 .0 % MeOH in DCM) to give tert-butyl 4-[cyclopropyl(1 ,2-oxazol-3-ylmethyl)amino]piperidine-1-carboxylate (150 mg, 58 %) as a liquid. LCMS (Method I): mlz 322 [M+H] (ES), at 4.92 mi UV active

References: [1]Patent: WO2017/21730,2017,A1 .Location in patent: Page/Page column 47.

31
[ 57684-71-6 ]
copper(l) cyanide [ No CAS ]
[ 55242-83-6 ]

Yield	Reaction Conditions	Operation in experiment
88.8%	In dimethyl sulfoxide; at 40℃;	In a three-necked flask, 200 mL of dimethyl sulfoxide and 30.0 g of 3-chloromethylisoxazole were added, and 21.5 g of copper cyanide was added.After heating to 40C, after completion of the reaction, 500 mL of water was added and the mixture was extracted with methylene chloride (100 mL x 3), and the organic phases were combined.Washed with saturated sodium bicarbonate, saturated brine, dried over anhydrous sodium sulfate,Concentration gave 24.5 g (88.8%) of 3-isoxazole acetonitrile.
	In dimethyl sulfoxide; at 30℃;	Add dimethyl sulfoxide and 3-chloromethylisoxazole to a three-necked flask, add cuprous cyanide, and heat to 30 C.After the reaction is completed, water is added, and the organic phase is extracted with dichloromethane, and washed with saturated sodium hydrogen carbonate.Wash with saturated brine and dry over anhydrous sodium sulfate.Concentrated to give 3-isoxazolylacetonitrile.

References: [1]Patent: CN103880765,2017,B .Location in patent: Paragraph 0027; 0038; 0043; 0048; 0049.
[2]Patent: CN109251180,2019,A .Location in patent: Paragraph 0014-0015; 0018-0019.

32
[ 57684-71-6 ]
[ 178970-86-0 ]
4-[(isoxazol-3-ylmethyl)sulfanyl]-6-methylfuro[3,4-c]pyridin-3(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium hydroxide; In water; N,N-dimethyl-formamide;Reflux;	General procedure: 10% aqueous KOH (3.1 ml, 5.6 mmol) was added to 6-methyl-4-thioxo-4,5-dihydrofuro[3,4-c]pyridin-3-one (4) (1.0 g, 5.6 mmol) in DMF (20 ml). The reaction mixture was heated (40-60C) until homogenous solution formed, and an equimolar amount of the corresponding alkylating reagent was added. The mixture was heated under reflux with stirring for 3-8 h, monitoring the progress of the reaction by TLC. After cooling in an ice bath, the crystalline product was filtered off, washed with H2O, and recrystallized from EtOH.

References: [1]Chemistry of Heterocyclic Compounds,2019,vol. 55,p. 1098 - 1103.
Khim. Geterotsikl. Soedin.,2019,vol. 55,p. 1098 - 1103,6.

33
[ 57684-71-6 ]
4-bromo-1H-pyrrolo[2,3-d]pyridine [ No CAS ]
C₁₁H₈BrN₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of 4-chloro-lH-pyrrolo-[3,2-c]-pyridine [60290-21-3] (2.0 g, 13.1 mmol) dissolved in DMF (30.5 mL, 0.944 g/mL, 393.2 mmol) at 0C was added portionwise sodium hydride (1.1 g, 28.8 mmol). The reaction mixture was allowed to reach rt and stirred 45 min, after which it was re-cooled to 0C and l-bromobutane (2.1 mL, 1.27 g/mL, 19.7 mmol) was added dropwise. The mixture was then allowed to reach rt and stirred overnight. NaHC03 sat solution was added and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with water and brine, then dried over MgS04 and concentrated in vacuo. The crude residue was purified by column chromatography (silica gel; gradient Heptane/EtOAc from 100/0 to 50 /50) to yield 1-1 (2.7 g, 98.7%) as a yellow liquid

References: [1]Patent: WO2019/243535,2019,A1 .Location in patent: Page/Page column 28-29; 37.

Historical Records

Technical Information

• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

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P101	If medical advice is needed,have product container or label at hand.
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Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
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

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CAS No.: 57684-71-6

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CAS No.: 57684-71-6

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[ 57684-71-6 ] Synthesis Path-Downstream 1~33

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