[ CAS No. 123222-09-3 ] {[proInfo.proName]}

Name: 123222-09-3|Methyl 2-(2-chloropyridin-3-yl)acetate|97%
Brand: Ambeed
SKU: A368579
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Quality Control of [ 123222-09-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 123222-09-3 ]

CAS No. :	123222-09-3	MDL No. :
Formula :	C₈H₈ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HGRQGJYEMNWDFM-UHFFFAOYSA-N
M.W :	185.61	Pubchem ID :	19771888
Synonyms :

Safety of [ 123222-09-3 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 123222-09-3 ]

* 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 [ 123222-09-3 ]

[ 123222-09-3 ] Synthesis Path-Downstream 1~24

1
[ 123222-09-3 ]
[ 79-20-9 ]
C₁₀H₉NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2005/13981, 2005, A1 Location in patent: Page/Page column 44

2
petrol-washed sodium hydride [ No CAS ]
[ 123222-09-3 ]
[ 107-31-3 ]
[ 77-78-1 ]
[ 123222-08-2 ]
(E)-methyl 2-[2-(2-methoxyphenoxy-phenoxy)pyridin-3-yl]-3-methoxypropenoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With potassium carbonate In N,N-dimethyl-formamide	7 EXAMPLE 7 EXAMPLE 7 This Example illustrates the preparation of (E)-methyl 2-[2-(2-methoxyphenoxy-phenoxy)pyridin-3-yl]-3-methoxypropenoate (Compound No. 128 of Table I). To an ice-cold stirred suspension of petrol-washed sodium hydride (1.04 g, 50% dispersion in oil, 22 mmol) in DMF (16 ml) was added a solution of methyl 2-chloropyrid-3-ylacetate (2 g, 11 mmol) and methyl formate (12.95 g, 0.22 mol) in DMF (8 ml). The reaction mixture was allowed to warm to room temperature and stirring continued until tlc analysis showed that no starting material remained (ca. 3 hours). The reaction mixture was poured into water and then acidified with dilute hydrochloric acid. The solution was extracted repeatedly with ether and the combined extracts dried, filtered and evaporated. The residue was redissolved in DMF and then treated with dimethyl sulphate (1.32 g, 10.5 mmol) and anhydrous potassium carbonate (1.52 g, 11 mmol) at room temperature. The reaction mixture was stirred for 2 hours, diluted with water and then repeatedly extracted with ether. The combined ether extracts were dried, filtered and evaporated to afford a yellow oil. Chromatrography on silica (eluent petrol-ether, 50:50) gave (E)-methyl 2-(2-chloropyrid-3-yl)-3-methoxypropenoate as a white waxy solid (0.9 g, 36%). Melting point: 39°-40° C. Infrared max.: 1711, 1638 cm-1. 1 H NMR delta: 3.74 (3H, s), 3.89 (3H, s), 7.21-7.26 (1H), 7.55-7.57 (1H), 7.60 (1H, s), 8.32-8.36 (1H).

Reference： [1]Current Patent Assignee: Syngenta (in: Sinochem Holdings); SINOCHEM HOLDINGS CORPORATION LTD - US5008276, 1991, A

3
petrol-washed sodium hydride [ No CAS ]
[ 123222-09-3 ]
[ 107-31-3 ]
[ 77-78-1 ]
[ 123222-08-2 ]
[ 114102-64-6 ]

Yield	Reaction Conditions	Operation in experiment
36%	With potassium carbonate In N,N-dimethyl-formamide	1 EXAMPLE 1 EXAMPLE 1 This example illustrates the preparation of (E)-methyl 2-(2-(3-fluorophenoxy)pyrid-3-yl)-3-methoxypropenoate ((IV), A=3-F, B=D=Y=H). To an ice-cold stirred suspension of petrol-washed sodium hydride (1.04 g, 50% dispersion in oil, 22 mmol) in DMF (16 ml) was added a solution of methyl 2-chloropyrid-3-ylacetate (2 g, 11 mmol) and methyl formate (12.95 g, 0.22 mol) in DMF (8 ml). The reaction mixture was allowed to warm to room temperature and stirring continued until TLC analysis showed that no starting material remained (ca 3 hours). The reaction mixture was poured into water and then acidified with dilute hydrochloric acid. The solution was extracted repeatedly with ether and the combined extracts dried, filtered and evaporated. The residue was redissolved in DMF and then treated with dimethyl sulphate (1.32 g, 10.5 mmol) and anhydrous potassium carbonate (1.52 g, 11 mmol) at room temperature. The reaction mixture was stirred for 2 hours, diluted with water and then repeatedly extracted with ether. The combined ether extracts were dried, filtered and evaporated to afford a yellow oil. Chromatography on silica (eluent petrol-ether, 50:50) gave (E)-methyl 2-(2-chloropyrid-3-yl)-3-methoxypropenoate as a white waxy solid (0.9 g, 36%); mp 39°-40° C.; Infrared max 1711, 1638 cm-1; 1 H NMR delta 3.74 (3H,s), 3.89 (3H,s), 7.21-7.26 (1H), 7.55-7.57 (1H), 7.60 (1H,s), 8.32-8.36 (1H).

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - US5039810, 1991, A

4
[ 67-56-1 ]
[ 61494-55-1 ]
[ 123222-09-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With acetyl chloride; at 70℃; for 18h;	INTERMEDIATE 13; r2-Chloropyridin-3-yl)acetic acid methyl ester; To a suspension of Intermediate 12 (3.88 g, 22.6 mmol) in methanol was added acetyl chloride (1.8 mL, 24.9 mmol) and the mixture heated at 700C for 18 hours. The solvents were removed in vacuo to give the title compound as a pale brown oil (4.63 g, quant). deltaH (DMSOd6) 8.35 (IH, dd, J4.7, 1.9 Hz), 7.88 (IH, dd, J 8.5, 1.9 Hz), 7.43 (IH, dd, J8.5, 4.7 Hz), 3.80 (2H, s), 3.65 (3H, s). LCMS (ES+) RT 2.40 minutes, 186 (M+H)+.
76%	With acetyl chloride; for 20h;Reflux;	Acetyl chloride (0.651 mL, 9.16 mmol) was added to a suspension of (2- chloropyridin-3-yl)acetic acid (1117) (1.048 g, 6.108 mmol) in MeOH (30 mL). The mixture was heated at reflux for 20 hours. The volatiles were removed in vacuo and the residue partitioned between OCM (100 mL) and sat. NaHC03 ( 100 mL). The layers were separated and the aqueous layer extracted with DCM (2x100 mL). The combined organic layers were washed with brine (100 mL), dried (Na2S0 ) and the solvent removed under reduced pressure to yield an oil which was purified by column chromatography on silica gel (0-40% EtOAc in petroleum benzine 40-60 C) to afford the title compound (1118) (0.863 g, 76%) as a pale yellow oil; NMR (400 MHz, dr D SO) delta 8.34 (dd, J = 4.8, 1.9 Hz, H), 7.88 (dd, J - 7.5, 1.9 Hz, 1 H), 7.43 (dd, J.= 7.5, 4.8 Hz, 1 H), 3.86 (s, 2H), 3.65 (s, 3H). LCMS Method C: rt 5.04 min; m/z 186 [M+H]+.
76%	With acetyl chloride; for 20h;Reflux;	Acetyl chloride (0.651 mL, 9.18 mmol) was added to a suspension of (2- chloropyridin-3-yi)acetic acid (1117) (1.048 g, 6.108 mmol) in MeOH (30 mL). The mixture was heated at reflux for 20 hours. The voiatiles were removed in vacuo and the residue partitioned between DCM (100 mL) and sat. NaHC03 (100 mL). The layers were separated and the aqueous layer extracted with DCM (2x100 mL). The combined organic layers were washed with brine (100 mL), dried (Na2S04) and the solvent removed under reduced pressure to yield an oil which was purified by column chromatography on silica gel (0-40% EtOAc in petroleum benzine 40-60 C) to afford the title compound (1118) (0.863 g, 76%) as a pale yellow oil; 1H NMR (400 MHz, d6~ DMSO) delta 8.34 (dd, J = 4.8, 1.9 Hz, 1 H), 7.83 (dd, J = 7.5, 1.9 Hz, 1 H), 7.43 (dd, J = 7.5, 4.8 Hz, 1 H), 3.86 (s, 2H), 3.65 (s, 3H). LC S Method C: rt 5.04 min; m/z 186 [M+H]+.

Reference： [1]Patent: WO2007/88345,2007,A1 .Location in patent: Page/Page column 24
[2]Patent: WO2012/110773,2012,A1 .Location in patent: Page/Page column 138; 139; 140
[3]Patent: WO2014/27199,2014,A1 .Location in patent: Page/Page column 141-142

5
[ 123222-09-3 ]
[ 945530-32-5 ]
2-[(2-fluoro-4-iodophenyl)amino]thieno[2,3-d]pyridine-3-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In dimethyl sulfoxide at 20 - 90℃; for 3.25h;	14 INTERMEDIATE 14; 2-[(2-Fluoro-4-iodophenyl)aminolthienor2,3-&lpyridine-3-carboxylic acid methyl ester; To a solution of Intermediate 13 (4.1 g, 22.1 mmol) and Intermediate 1 (6.16 g, 22.1 mmol) in dry DMSO under nitrogen was added sodium hydride (1.05 g, 24.3 mmol, 60 wt % dispersion in mineral oil). The mixture was stirred at room temperature for 15 minutes then heated to 900C for 3 hours. The reaction was cooled, then poured onto iced water (200 mL). The aqueous phase was extracted with EtOAc (3 x 200 mL), the combined organics washed with brine, dried (MgSO4), filtered and the solvents removed in vacuo. The sticky yellow solid was triturated with ethanol to give a fine yellow solid which was collected by filtration, washed with diethyl ether and dried under suction to give the title compound as a pale yellow solid (1.73 g). δϖ (DMSO-d6) 10.30 (IH, s), 8.36-8.31 (2H, m), 7.87 (IH, dd, J 1.9, 10.0 Hz), 7.70 (IH, d, J6.6 Hz), 7.51 (IH, t, /8.5 Hz), 7.42 (IH, dd, J5.7, 8.1 Hz), 3.94 (3H, s). LCMS (ES+) RT 4.00 minutes, 429 (MH-H)+.

Reference： [1]Current Patent Assignee: UCB - WO2007/88345, 2007, A1 Location in patent: Page/Page column 24

6
[ 101012-32-2 ]
[ 123222-09-3 ]