113975-32-9|N-(4-Iodopyridin-3-yl)pivalamide| Ambeed

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Quality Control of [ 113975-32-9 ] Purity: 95+% SDS Specification

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Product Details of [ 113975-32-9 ]

CAS No. :	113975-32-9
Formula :	C₁₀H₁₃IN₂O
M.W :	304.13
SMILES Code :	CC(C)(C)C(=O)NC1=CN=CC=C1I
MDL No. :	MFCD06659003
InChI Key :	MWRKADKNFCJKNN-UHFFFAOYSA-N
Pubchem ID :	10447729

Safety of [ 113975-32-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 113975-32-9 ]

* 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 [ 113975-32-9 ]

[ 113975-32-9 ] Synthesis Path-Downstream 1~35

1
[ 75-97-8 ]
[ 113975-32-9 ]
[ 113975-40-9 ]

References: [1]Journal of Organic Chemistry,1988,vol. 53,p. 2740 - 2744.

2
[ 1993-03-9 ]
[ 113975-32-9 ]
[ 146140-96-7 ]

References: [1]Tetrahedron,1993,vol. 49,p. 49 - 64.
[2]Tetrahedron,1993,vol. 49,p. 49 - 64.

3
[ 5720-06-9 ]
[ 113975-32-9 ]
[ 131653-65-1 ]

References: [1]Tetrahedron,1993,vol. 49,p. 49 - 64.
[2]Journal of the Chemical Society. Perkin transactions I,1990,p. 2611 - 2612.

4
[ 201230-82-2 ]
[ 113975-32-9 ]
[ 156488-90-3 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 3197 - 3200.

5
[ 70298-88-3 ]
[ 113975-32-9 ]

Yield	Reaction Conditions	Operation in experiment
70%		The reaction was performed according to a procedure in the literature (J. Org. Chem. 1988, 53, 2740-2744). A 3 L three-neck round-bottom flask was equipped with a mechanical stirrer, thermocouple, nitrogen inlet, and drying tube and placed in a cooling bath. The flask was charged with 2,2-dimethyl-N-(3-pyridyl)propanamide (42, 40 g), tetramethylethylenediamine (TMEDA, 84 mL) and THF (1400 mL), and stirring was initiated. The reaction mixture was cooled to -78 C. A suspension formed. n-BuLi (224 mL) was added over at least a 15 minute period at a rate to keep the temperature below -65 C. The reaction mixture was stirred continually at -78 C. for 15 minutes before being stirred for 2 h at -10 C. A yellow to white precipitate slowly developed. The reaction mixture was cooled back to -78 C. A solution of iodine (142 g) in THF (480 mL) was added over 30 minutes. The temperature increased from -78 C. to -65 C. The reaction mixture was stirred continually for 2 h at -78 C. The reaction mixture was continually stirred at -78 C. until the reaction was deemed complete, i.e., upon disappearance of 2,2-dimethyl-N-(3-pyridyl)propanamide (42). If reaction was not complete, it was stirred continually at -78 C. for additional 1 h then monitored again. The reaction was monitored by TLC (SiO2, [7:3] EtOAc:Hept, UV, two developments) by partitioning an aliquot of the reaction mixture (1 mL) between EtOAc (1 mL) and saturated ammonium chloride solution (3 mL), agitating, allowing the layers to separate, and spotting the organic layer. The starting material (2,2-dimethyl-N-(3-pyridyl)propanamide, 42) had an RF of 0.25, and the product (N-(4-iodo(3-pyridyl))-2,2-dimethylpropanamide, 43) had an RF of 0.33. Typically, the reaction conversion was 80% to product based on TLC. Materials used to synthesize N-(4-iodo(3-pyridyl))-2,2-dimethylpropanamide (43) are shown in Table 34. To isolate the product (N-(4-iodo(3-pyridyl))-2,2-dimethylpropanamide, 43), the reaction mixture was poured into a saturated (10%) NH4Cl solution (100 mL). The mixture was extracted with ethyl acetate (2×500 mL). The combined organic layer was washed with a saturated (10%) sodium thiosulfate solution (2×100 mL) to remove excess iodine and brine (200 mL). The organic layer was dried over MgSO4 and charcoal, filtered through glass fiber filter paper, and concentrated to dryness. The above crude material was purified by passing through a silica plug (4 g of SiO2/1 g of crude mixture), and eluting the plug with 10-50% ethyl acetate in heptanes. All fractions that contained compound were combined and concentrated under reduced pressure at 45 C. to yield a beige solid. The solid was dried under vacuum at 25 C. for a minimum of 5 hours.N-(4-iodo(3-pyridyl))-2,2-dimethylpropanamide (43, lot No. 1358-77-1) was a beige solid, synthesized with a yield of 48 g (70%). N-(4-iodo(3-pyridyl))-2,2-dimethylpropanamide (43) was analyzed using HPLC (MPP-LC1, 240 nm), and according to results, it was 95.9% pure. 1H-NMR (300 MHz, CDCl3) was used to confirm the identity of N-(4-iodo(3-pyridyl))-2,2-dimethylpropanamide (43).
38%		A solution of 2,2-dimethyl-N-pyridin-3-ylpropanamide [(1g, 5.61mmol), J. Org. Chem, 48(20), 3401;1998] in tetrahydrofuran (10mL) and diethyl ether (30mL) was cooled to -78C and TMEDA (2.1mL, 14mmol) and nbutyl lithium (1.6M in hexane, 8.8mL, 14mmol,) were added dropwise. The mixture was stirred for 15 minutes and was then warmed to -10C and stirred for a further 2 hours. The reaction mixture was again cooled to -78C and a solution of iodine (3.56g, 14mmol) in tetrahydrofuran (10mL) was added dropwise. The resulting slurry was stirred at -78C for 2 hours. The mixture was warmed to 0C and was quenched with saturated aqueous sodium thiosulfate solution (50mL). The phases were separated and the aqueous phase was extracted with dichloromethane (2x30mL). The combined organic phase was dried over magnesium sulfate and concentrated in vacuo. Purification of the residue by column chromatography on silica gel, eluding with pentane:ethyl acetate, 50:50 afforded the title compound as a yellow solid in 38% yield, 655mg. 1H-NMR(CDCl3, 400MHz) δ: 1.38(s, 9H), 7.65(bs, 1H), 7.73(d, 1H), 7.97(d, 1H), 9.35(s, 1H) MS APCI+ m/z 305 [MH]+
37%		To a solution of 2,2-dimethyl-N-pyridin-3-yl-propionamide (7 g, 39.32 mmol) in THF (50 mL) was added TMEDA (20 mL, CAS RN 110-18-9) at 25 C. The mixture was cooled to-70 C., n-butyllithium was added (66 mL, 1.6M solution in n-hexane, CAS RN 109-72-8) within a period of 30 min under an atmosphere of argon. The reaction mixture was allowed to stir at -15 C. for 1 h, followed by another 1 h at 0 C. The reaction mixture was re-cooled to -70 C., then a solution of iodine (29.2 g, 115.1 mmoL) in THF (120 mL) was added slowly during 1 h, and the resultant mixture was allowed to stir at 25 C. for 16 h. Water and saturated aqueous Na2S2O3 solution was added to the mixture, and then extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford the crude residue which was purified by column chromatography over silica gel (40% EtOAc in n-hexane) to give the title compound. Pale yellow solid (800 mg, 37%). MS (ESI): m/z=305.4 [M+H]+.

23%		Preparation 5; N-(4-Iodo-pyridin-3-yl)-2,2-dimethyl-propionamide; Equip a 250 mL 3 -neck round bottom flask with: a magnetic stirrer, a thermocouple, a dry ice/acetone bath, a nitrogen atmosphere, and an addition funnel. Charge 2,2-dimethyl-N-pyridin-3-yl-propionamide (3.0 g, 16.8 mmol), diethyl ether (67 mL), tetramethylene diamine (4.68 g, 6.08 mL, 40.3 mmol). Cool the reaction to -78 0C. Add slowly via glass syringe w-butyllithium (2.5 M solution in hexane, 16.2 mL, 40.3 mmol) over 10 min. Allow the reaction to warm to -13 0C over 2 hours. Cool the <n="10"/>-9-reaction to -78 0C. Add an iodine solution (8.5 g, 33.6 mmol in 20 mL THF) to the reaction via the addition funnel and mix 2.5 hours at -68 0C. Quench the reaction by the addition of saturated aqueous NH4Cl solution (40 mL). Extract with ethyl acetate (100 mL) and discard the aqueous phase. Wash the organic layer with a saturated aqueous sodium thiosulfate solution (100 mL) and saturated aqueous sodium chloride. Dry the organic phase over sodium sulfate and filter. Concentrate in vacuo to give brown oil. Chromatograph on silica (80 g) eluting with a gradient of 100 % dichloromethane to 70 % ethyl acetate /30 % dichloromethane to afford the title compound (1.19 g, 23 %). MS (ES) m/z 305 [M+ 1]+
23%		Preparation 65N-(4-Iodo-pyridin-3-yl)-2,2-dimethyl-propionamide Equip a 250-mL round bottom flask with a magnetic a stirrer, a thermocouple, a dry ice/acetone bath, a ν2 atmosphere, and an addition funnel. Charge with 2,2-dimethyl- N-pyridin-3-yl-propionamide (3.0 g, 16.8 mmol), diethylether (67 mL), and tetramethylene diamine (4.68 g, 6.08 mL, 40.3 mmol). Cool the reaction to -78 0C. Add slowly via glass syringe w-butyllithium (2.5 M solution in hexane, 16.2 mL, 40.3 mmol) over 10 min. Warm the reaction to -13 0C over 2 h. Cool the reaction to -78 0C. Prepare an iodine solution (I2 8.5 g, 33.6 mmol in THF (20 mL)). Add the iodine solution to the reaction via the addition funnel and stir 2.5 h. at -68 0C. Quench the reaction with the addition of a saturated NH4Cl solution (40 mL) and transfer into a separatory funnel. Add ethyl acetate (100 mL). Extract and discard the lower aqueous phase. Wash the organic layer with a saturated sodium thiosulfate solution (100 mL) and extract. Wash the organic phase with saturated aqueous sodium chloride and extract. Dry the organic phase over Na2SO4 and filter. Concentrate the product via rotary evaporation. Chromatograph on silica (80 g) eluting with gradient of 100 % DCM to 70 % ethyl acetate/30 % DCM to afford 1.19 g (23 %) of the title compound. MS (ES) mk 306 [M+ 1]+.
		To a solution of 2,2-dimethyl-N-pyridin-3-yl-propionamide (7 g, 39.32 mmol) in THF (50 mL) was added TMEDA (20 mL, CAS RN 110-18-9) at 25 C. The mixture was cooled to -70 C, n-butyllithium was added (66 mL, 1.6M solution in n-hexane, CAS RN 109-72-8) within a period of 30 min under an atmosphere of argon. The reaction mixture was allowed to stir at -15 C for 1 h, followed by another 1 h at 0 C. The reaction mixture was re-cooled to -70 C, then a solution of iodine (29.2 g, 115.1 mmoL) in THF (120 mL) was added slowly during 1 h, and the resultant mixture was allowed to stir at 25 C for 16 h. Water and saturated aqueous Na2S203 solution was added to the mixture, and then extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2S04, filtered and concentrated in vacuo to afford the crude residue which was purified by column chromatography over silica gel (40% EtOAc in n-hexane) to give the title compound. Pale yellow solid (800 mg, 37%). MS (ESI): m/z = 305.4 [M+H]+.

References: [1]Patent: US2009/306121,2009,A1 .Location in patent: Page/Page column 24-25; sheet 16.
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 6519 - 6534.
[3]Patent: EP1595881,2005,A1 .Location in patent: Page/Page column 57.
[4]Patent: US2012/232051,2012,A1 .Location in patent: Page/Page column 61.
[5]Patent: WO2008/76704,2008,A1 .Location in patent: Page/Page column 8-9.
[6]Patent: WO2008/144222,2008,A2 .Location in patent: Page/Page column 26.
[7]Journal of the Chemical Society. Perkin transactions I,1990,p. 2611 - 2612.
[8]Journal of Organic Chemistry,1988,vol. 53,p. 2740 - 2744.
[9]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 11 - 16.
[10]Tetrahedron Letters,2004,vol. 45,p. 8569 - 8573.
[11]Dalton Transactions,2011,vol. 40,p. 4217 - 4222.
[12]Patent: WO2012/117000,2012,A1 .Location in patent: Page/Page column 128.

6
[ 119485-59-5 ]
[ 113975-32-9 ]
thieno<3,2-c><1,7>naphthyridine [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 11 - 16.

7
[ 113975-32-9 ]
[ 103681-98-7 ]
[ 131653-66-2 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 2611 - 2612.
[2]Journal of Medicinal Chemistry,2003,vol. 46,p. 3138 - 3151.

8
[ 113975-32-9 ]
[ 103698-26-6 ]
[ 131653-67-3 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 2611 - 2612.

9
[ 113975-32-9 ]
[ 131653-74-2 ]
[ 131653-68-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 2611 - 2612.

10
[ 113975-32-9 ]
[ 120789-51-7 ]
1-[2-(tert-Butyl-dimethyl-silanyl)-3-hydroxymethyl-pyrrolo[2,3-c]pyridin-1-yl]-2,2-dimethyl-propan-1-one [ No CAS ]

References: [1]Tetrahedron Letters,1993,vol. 34,p. 2823 - 2826.

11
[ 113975-32-9 ]
[ 146140-95-6 ]
2,2-dimethyl-N-(4-(2-pivaloylaminophenyl)-3-pyridyl)propanamide [ No CAS ]

References: [1]Tetrahedron,1993,vol. 49,p. 49 - 64.

12
[ 113975-32-9 ]
[ 105752-11-2 ]

Yield	Reaction Conditions	Operation in experiment
92%		iV-(4-Iodo-pyridin-3-yl)-2,2-dimethyl-propionamide (20.00 g, 65.76 mmol) was charged to a 2 L round-bottom flask and 24% sulfuric acid in water (640 mL) was added carefully. The mixture was heated to 100 C for 4 hours. The reaction was determined complete by analyitical HPLC. The mixture was allowed to cool to room temperature and then carefully adjusted to pH 7-8 with 4Ν NaOH (approximately 700 mL). Saturated sodium bicarbonate was added to the mixture and the product extracted into dichloromethane (3 X 500 mL). The organic layers were combined and concentrated to give 3-amino-4-iodo- pyridine (13.3 g, 92%).
90%	With sulfuric acid; In water; for 1h;Heating / reflux;	The product of preparation 22 (4.69g, 15.4mmol) and dilute sulphuric acid (24%, 120mL) were heated under reflux for 1 hour. The mixture was then cooled, basified with solid sodium hydrogen carbonate to pH8 and extracted with dichloromethane (3x200mL). The combined organic solutions were dried over magnesium sulfate and concentrated in vacuo. Purification of the residue by column chromatography on silica gel, eluding with dichloromethane:methanol, 100:0 to 90:10, afforded the title compound as a brown solid in 90% yield, 3.04g. 1H-NMR(CDCl3, 400MHz) δ: 4.11 (bs, 2H), 7.56(d, 1H), 7.61 (d, 1H), 8.05(s, 1H) MS APCI+ m/z 221 [MH]+
75%		The reaction was performed according to a procedure in the literature (Tetrahedron Lett. 2005, 46, 6363). A 1 L three-neck round-bottom flask was equipped with a mechanical stirrer, thermocouple, nitrogen inlet, and drying tube and placed in a heating mantle. The flask was charged with N-(4-iodo(3-pyridyl))-2,2-dimethylpropanamide (43, 45 g) and 25% sulfuric acid (270 mL). The solubility of starting material in 25% sulfuric acid was very high and formed light yellow clear solution. The reaction mixture was heated to 80 C. for 8 h. The reaction mixture was stirred continually at 80 C. until deemed to be complete, i.e., upon complete disappearance of starting material (N-(4-iodo(3-pyridyl))-2,2-dimethylpropanamide, 43). If reaction was not complete, stirring was continued at 80 C. for additional 6 h then monitored again, and repeated until complete. Typically, reaction was complete within 4-6 h. The reaction was monitored by TLC (SiO2, 100% EtOAc, UV) by partitioning an aliquot of reaction mixture (1 mL) between 50% NaOH solution (2 mL) and EtOAc (4 mL), agitating, allowing the layers to separate, and spotting the organic layer on TLC. The starting material (N-(4-iodo(3-pyridyl))-2,2-dimethylpropanamide, 43) had an RF of 0.55, and the product (4-iodo-3-pyridylamine, 44) had an RF of 0.35. Materials used to synthesize 4-iodo-3-pyridylamine (44) are shown in Table 35.To isolate the product (4-iodo-3-pyridylamine, 44), the flask was cooled to -10 C. and the mixture was cautiously basified (pH 10-11) with 50% NaOH solution (45 g) while maintaining a temperature below 10 C. Additional ethyl acetate (200 mL) was added, the reaction was stirred for 10 minutes, and the layers were allowed to separate. The organic layer was collected, and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layer was dried over MgSO4 and charcoal, filtered through a glass fiber filter paper, and concentrated to dryness. The residue was diluted with MTBE (50 mL) and the solids were filtered, rinsing with MTBE (10 mL). The product was air-dried for 2 h and then dried under high vacuum at room temperature to constant weight.4-Iodo-3-pyridylamine (44, lot No. 1358-86-1) was an off-white solid, synthesized with a yield of 24 g (75%). 4-Iodo-3-pyridylamine (44) was analyzed using HPLC (PLX-LC3, 220), and according to results, it was 100% pure. 1H-NMR (300 MHz, CDCl3) was used to confirm the identity of 4-iodo-3-pyridylamine (44).

		3-(tert-Butylcarbonylamino)-4-iodo-pyridine (20.00 g, 65.76 mmol) was charged to a 2 L round-bottom flask, and sulfuric acid, 24% in water (640 mL) was carefully added. The reaction was heated to 100 0C. After 4 hours, the reaction was shown to be complete as determined by HPLC. After cooling to room temperature, the solution was carefully neutralized with 4 M NaOH until a pH of 7-8 was achieved. Saturated bicarbonate was added to the reaction mixture, and the product extracted into dichloromethane (3 X 500 mL). The organic layers were combined and concentrated to give 13.3 g of 3-amino-4-iodo-pyridine.
		A solution of N-(4-iodo-pyridin-3-yl)-2,2-dimethyl-propionamide (6 g, 19.73 mmol) in aqueous 3M HCl (50 mL) was heated to 100 C. for 18 hours. After the completion of reaction, the reaction mass was washed with EtOAc. Under cooling the pH of the aqueous layer was adjusted to pH 9 using solid Na2CO3 and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford 4-iodo-pyridin-3-ylamine (3.2 g crude, 73%) as a brown sticky solid that was used in the next step without further purification.
		A solution of N-(4-iodo-pyridin-3-yl)-2,2-dimethyl-propionamide (6 g, 19.73 mmol) in aqueous 3M HC1 (50 mL) was heated to 100 C for 18 hours. After the completion of reaction, the reaction mass was washed with EtOAc. Under cooling the pH of the aqueous layer was adjusted to pH 9 using solid Na2C03 and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2S04, filtered, and concentrated in vacuo to afford 4-iodo-pyridin-3-ylamine (3.2g crude, 73%) as a brown sticky solid that was used in the next step without further purification.

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 6519 - 6534.
[2]Patent: WO2006/86609,2006,A2 .Location in patent: Page/Page column 154.
[3]Patent: EP1595881,2005,A1 .Location in patent: Page/Page column 57.
[4]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 11 - 16.
[5]Tetrahedron Letters,2004,vol. 45,p. 8569 - 8573.
[6]Patent: US2009/306121,2009,A1 .Location in patent: Page/Page column 25-26; sheet 16.
[7]Patent: WO2006/86609,2006,A2 .Location in patent: Page/Page column 155.
[8]Dalton Transactions,2011,vol. 40,p. 4217 - 4222.
[9]Patent: US2012/232051,2012,A1 .Location in patent: Page/Page column 61.
[10]Patent: WO2012/117000,2012,A1 .Location in patent: Page/Page column 128.
[11]Chemistry - A European Journal,2012,vol. 18,p. 16358 - 16368.

13
[ 113975-32-9 ]
[ 67-64-1 ]
[ 113975-35-2 ]

References: [1]Journal of Organic Chemistry,1988,vol. 53,p. 2740 - 2744.

14
[ 113975-32-9 ]
[ 98-80-6 ]
[ 131653-64-0 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 2611 - 2612.

15
2-tert-butyl-5-(tri-n-butylstannyl)pyrido[3,4-d]pyrimidin-4(3-tri-n-butylstannyl)-one [ No CAS ]
[ 113975-32-9 ]
2-tert-butyl-5-phenylpyrido[3,4-d]pyrimidin-4(3H)-one [ No CAS ]
2-tert-butyl-5-[3-(pivaloylamino)-4-pyridyl]pyrido[3,4-d]pyrimidin-4(3H)-one [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2006,vol. 43,p. 1497 - 1503.

16
[ 462-08-8 ]
[ 113975-32-9 ]