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[ CAS No. 717843-48-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 717843-48-6
Chemical Structure| 717843-48-6
Chemical Structure| 717843-48-6
Structure of 717843-48-6 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 717843-48-6 ]

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Product Details of [ 717843-48-6 ]

CAS No. :717843-48-6 MDL No. :MFCD08059560
Formula : C7H5BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :ARSYSTQQVJUEBW-UHFFFAOYSA-N
M.W : 197.03 Pubchem ID :21952747
Synonyms :

Calculated chemistry of [ 717843-48-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.62
TPSA : 36.68 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.8
Log Po/w (XLOGP3) : 2.0
Log Po/w (WLOGP) : 2.02
Log Po/w (MLOGP) : 0.89
Log Po/w (SILICOS-IT) : 2.44
Consensus Log Po/w : 1.83

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.77
Solubility : 0.338 mg/ml ; 0.00172 mol/l
Class : Soluble
Log S (Ali) : -2.4
Solubility : 0.79 mg/ml ; 0.00401 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.35
Solubility : 0.0872 mg/ml ; 0.000443 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.79

Safety of [ 717843-48-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 717843-48-6 ]

* 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 [ 717843-48-6 ]

[ 717843-48-6 ] Synthesis Path-Downstream   1~67

  • 1
  • [ 444721-86-2 ]
  • [ 717843-48-6 ]
  • [ 760207-75-8 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In dichloromethane; toluene; Example 176 (7bR,11aS)-N-(2-Cyano-6-methyl-3-pyridinyl)-1,2,7b,8,9,10,11,11a-octahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-6-amine, bis hydrochloride salt A solution of tert-butyl (7bR,11aS)-6-amino-1,2,7b,10,11,11a-hexahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8H)-carboxylate from Example 56, Part B (300 mg, 0.89 mmol), <strong>[717843-48-6]2-cyano-3-bromo-6-methylpyridine</strong> (200 mg, 1.02 mmol) and cesium carbonate (565 mg, 1.73 mmol) in anhydrous toluene (10 mL) was stirred under an argon atmosphere in a sealable test tube. The mixture was degassed with argon. [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium (II), complex with dichloromethane (35 mg, 0.043 mmol) was added and the reaction was sealed and heated at 160 C. in a microwave oven for 3600 sec. The reaction mixture was cooled, filtered through a pad of silica gel and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 10-50% EtOAc/hexanes) provided tert-butyl (7bR,11aS)-6-(2-cyano-6-methyl-3-pyridinyl)-amino-1,2,7b,10,11,11a-hexahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8H)-carboxylate.
With caesium carbonate; In dichloromethane; toluene; Example 176 (7bR,11aS)-N-(2-Cyano-6-methyl-3-pyridinyl)-1,2,7b,8,9,10,11,11 a-octahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-6-amine, bis hydrochloride salt A solution of tert-butyl (7bR,11aS)-6-amino-1,2,7b,10,11,11a-hexahydro-4H-[1,4] oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8H)-carboxylate from Example 56, Part B (300 mg, 0.89 mmol), <strong>[717843-48-6]2-cyano-3-bromo-6-methylpyridine</strong> (200 mg, 1.02 mmol) and cesium carbonate (565 mg, 1.73 mmol) in anhydrous toluene (10 mL) was stirred under an argon atmosphere in a sealable test tube. The mixture was degassed with argon. [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium (II), complex with dichloromethane (35 mg, 0.043 mmol) was added and the reaction was sealed and heated at 160 C. in a microwave oven for 3600 sec. The reaction mixture was cooled, filtered through a pad of silica gel and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 10-50% EtOAc/hexanes) provided tert-butyl (7bR,11aS)-6-(2-cyano-6-methyl-3-pyridinyl)-amino-1,2,7b,10,11,11a-hexahydro-4H-[1,4]oxazepino[6,5,4-hi]pyrido[4,3-b]indole-9(8H)-carboxylate.
  • 2
  • [ 31181-64-3 ]
  • [ 7677-24-9 ]
  • [ 717843-48-6 ]
YieldReaction ConditionsOperation in experiment
85% With triethylamine; In acetonitrile; for 12h;Inert atmosphere; Reflux; b. Compound 2 is 5-bromo-2-methyl-N-oxopyridine 1.0 g (5.4 mmol) dissolved in acetonitrile under nitrogen protection.In 20 ml of the liquid, 2.1 g of trimethylsilyl cyanide (21.6 mmol) and 2.2 ml of triethylamine (16.2 mmol) were successively added. After refluxing for 12 hours, the organic solvent was removed and the medium pressure preparative chromatography was used as COMBIFLASH. The mobile phase was: The volume ratio of 1:10 ethyl acetate: petroleum ether purification to give compound 3 is 3-bromo-6-methyl-2-cyanopyridine, yield 85%, 0.9g;
85% With triethylamine; In acetonitrile; for 12h;Inert atmosphere; Reflux; Compound 2 was 5-bromo-2-methyl-N-oxypyridine 1.0 g (5.4 mmol) dissolved in acetonitrile under nitrogen atmosphere.Into 20 ml of liquid, 2.1 g (21.6 mmol) of trimethylcyanosilane and 2.2 ml (16.2 mmol) of triethylamine were added in this order, and refluxed for 12 hours.After that, the organic solvent was removed, and the medium-pressure preparative chromatogram was COMBIFLASH, mobile phase: ethyl acetate: petroleum ether in a volume ratio of 1:10.Purification, the compound 3 was obtained as 3-bromo-6-methyl-2-cyanopyridine, the yield was 85%, 0.9 g;
78% With triethylamine; In acetonitrile; at 100℃; (2) in the 1L acetonitrile (ACN) in the solvent by adding 2 - bromo -6 - methyl pyridine oxide (44g, 0.23 muM), trimethylsilyl cyanide (TMSCN) (92.7g, 0 . 94 muM), triethylamine (TEA) (70.9g, 0.7 muM), mixture in 100 C stirring the reaction overnight under the condition; cooling to room temperature, concentrated hangs steams after purification through silica gel solvent (petroleum ether/ethyl acetate flow matching ratio (PE/EA)=10:1), resulting in white or white solid 3 - bromo -6 - methyl -2 - cyano pyridine, yield is 78%, about 35g.
71% With triethylamine; In acetonitrile; at 100℃;Inert atmosphere; A mixture of 180 5-bromo-2-methylpyridine 1-oxide 17b (20.5 g, 109 mmol), 182 trimethylsilanecarbonitrile (43.25 g, 436 mmol), 153 triethylamine (33.0 g, 327 mmol) and 149 acetonitrile (500 mL) was heated to 100 C. and stirred overnight. The mixture was cooled to room temperature and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=1/1) to give the target 183 compound 3-bromo-6-methylpicolinonitrile 17c (17.1 g, yellow solid). Yield: 71%. MS m/z (ESI): 197/199[M+1]
With triethylamine; In acetonitrile; at 100℃; To a solution of 5-bromo-2-methylpyridine 1-oxide (from step 1) (1.0 eq.) in acetonitrile (0.2 M) was added trimethylsilyl cyanide (TMSCN) (4.0 eq.) and triethylamine (3.0 eq.). The reaction was heated at 100 C. overnight. After cooling to room temperature, the solvent was concentrated en vacuo, and the residue was purified by a COMBIFLASH system (ISCO) using 0-50% ethyl acetate in hexane to give 3-bromo-6-methylpicolinonitrile.
With triethylamine; In acetonitrile; at 100℃; To a solution of 5-bromo-2-methylpyridine 1-oxide (from step 1) (1.0 eq.) in acetonitrile (0.2 M) was added tnmethylsilyl cyanide (TMSCN) (4.0 eq.) and tnethylamine (3.0 eq.). The reaction was heated at 1000C overnight. After cooling to room temperature, the solvent was concentrated en vacuo, and the residue was purified by a COMBIFLASH system (ISCO) using 0-50% ethyl acetate in hexane to give 3-bromo-6-methylpicolinonit?le.

  • 3
  • [ 717843-48-6 ]
  • [ 115377-94-1 ]
  • [ 1186635-20-0 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 100℃; A solution of 2-(tert-butoxycarbonylamino)phenylboronic acid (1.0 eq.) and <strong>[717843-48-6]3-bromo-6-methylpicolinonitrile</strong> (from step 2) (1.0 eq.) in toluene (0.44 M) was mixed with tetrakis(triphenyl-phosphine)palladium (5 mol %) and 2N aqueous potassium carbonate solution (2.0 eq.). The reaction was heated to 100 C. and stirred overnight. After cooling to ambient temperature, the reaction content was diluted with 2% methanol in dichloromethane and water. The two phases were separated, and the aqueous layer was extracted twice with 2% methanol in dichloromethane. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude product was purified by flash chromatography on a COMBIFLASH system (ISCO) using 0-70% ethyl acetate in hexane to give 3-methylbenzo[f][1,7]naphthyridin-5-amine as a yellow solid. 1H NMR (methanol d-4): delta 8.85 (d, 1H), 8.38 (d, 1H), 7.72 (d, 1H), 7.53-7.61 (m, 2H), 7.34-7.38 (dd, 1H), 2.76 (s, 3H). LRMS [M+H]=210.1
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 100℃; A solution of 2-(tetaut-butoxycarbonylamino)phenylboronic acid (1.0 eq.) and <strong>[717843-48-6]3-bromo-6-methylpicolinonitrile</strong> (from step 2) (1.0 eq.) in toluene (0.44 M) was mixed with tetrakis(t?phenyl-phosphine)palladium (5 mol%) and 2N aqueous potassium carbonate solution <n="180"/>(2.0 eq.). The reaction was heated to 1000C and stirred overnight. After cooling to ambient temperature, the reaction content was diluted with 2% methanol in dichloromethane and water. The two phases were separated, and the aqueous layer was extracted twice with 2% methanol in dichloromethane. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude product was purified by flash chromatography on a COMBIFLASH system (ISCO) using 0-70% ethyl acetate in hexane to give 3- methylbenzo[f][l,7]naphthyridin-5-amine as a yellow solid. 1H NMR (methanol d-4): delta 8.85 (d, IH), 8.38 (d, IH), 7.72 (d, IH), 7.53-7.61 (m, 2H), 7.34-7.38 (dd, IH), 2.76 (s, 3H). LRMS [M+H] = 210.1
  • 4
  • [ 1722-12-9 ]
  • [ 717843-48-6 ]
  • [ 1228188-17-7 ]
YieldReaction ConditionsOperation in experiment
Isopropylmagnesium chloride-LiCl (37.9 ml, 36.5 mmol) was added portion wise (in overall 10 min) to a solution of <strong>[717843-48-6]3-bromo-6-methyl-2-pyridinecarbonitrile</strong> (4 g, 20.30 mmol) in THF (150 ml) cooled to -70 C. (internal temperature). The reaction was kept to that temperature for 15 min. Then it was allowed to gently warm up to -40 C. in overall 1 hour. Then, it was cooled to -78 C. and zinc chloride (3.32 g, 24.36 mmol) was added. The resulting mixture was allowed to warm up to room temperature in 1 hour. Pd(Ph3P)4 (2.346 g, 2.030 mmol), 2-chloropyrimidine (3 g, 26.2 mmol) were added and the mixture was refluxed (external temperature 100 C.) until complete consumption of starting chloropyrimidine (3 hours). The reaction mixture was cooled to room temperature and poured into water (200 ml) cooled to 10 C. It was then extracted with EtOAc (5×200 mls). The collected organic phases, containing large amount of colloid material and water, were washed with brine (200 ml). The water phase was filtered over a gouch, and the solid material was washed with further EtOAc (2×300 mls). The collected organic phases were dried overnight over Na2SO4, filtered and concentrated to give (7 g) the crude material which was purified (Biotage Sp1 over a 240 g Silica Anolgix column, with a 25 g pre-column) to give the title compound D68 as yellow solid (1.8 g). UPLC (Acid GEN_QC SS): rt=0.58 minutes, peak observed: 197 (M+1). C11H8N4 requires 196.
Isopropylmagnesium chloride-LiCl (37.9 ml, 36.5 mmol) was added portion wise (in overall 10 min) to a solution of <strong>[717843-48-6]3-bromo-6-methyl-2-pyridinecarbonitrile</strong> (4 g, 20.30 mmol) in THF (150 ml) cooled to -70 0C (internal temperature). The reaction was kept to that temperature for 15 min. Then it was allowed to gently warm up to -40 0C in overall 1 hour. Then, it was cooled to -78 0C and zinc chloride (3.32 g, 24.36 mmol) was added. The resulting mixture was allowed to warm up to room temperature in 1 hour. Pd(PtLsP)4 (2.346 g, 2.030 mmol), 2-chloropyrimidine (3 g, 26.2 mmol) were added and the mixture was refluxed (external temperature 100 0C) until complete consumption of starting chloropyrimidine (3 hours). The reaction mixture was cooled to room temperature and poured into water (200 ml) cooled to 10 0C. It was then extracted with EtOAc (5 x 20OmIs). The collected organic phases, containing large amount of colloid material and water, were washed with brine (200 ml). The water phase was filtered over a gouch, and the solid material was washed with further EtOAc (2 x 30OmIs). The collected organic phases were dried overnight over Na2SO4, filtered and concentrated to give (7 g) the crude material which was purified (Biotage SpI over a 240 g Silica Anolgix column, with a 25 g pre- column) to give the title compound D63 as yellow solid (1.8 g). UPLC (Acid GEN_QC_SS): rt = 0.58 minutes, peak observed: 197 (M+l). CnH8N4 requires 196.
Description 58: 6-methyl-3-(2-pyrimidinyl)-2-pyridinecarbonitrile (D58); Isopropylmagnesium chloride LiCl (37.9 ml, 36.5 mmol) was added portion wise (in overall 10 minutes) to a solution of <strong>[717843-48-6]3-bromo-6-methyl-2-pyridinecarbonitrile</strong> (4 g, 20.30 mmol) in THF (150 ml) cooled to -70 0C (internal temperature). The reaction was kept to that temperature for 15 minutes, then it was allowed to gently warm up to -40 0C in overall 1 hour. Then, it was cooled to -78 0C and zinc chloride (3.32 g, 24.36 mmol) was added. The resulting mixture was allowed to warm up to room temperature in 1 hour. Pd(Ph3P)4 (2.346 g, 2.030 mmol), 2-chloropyrimidine (3 g, 26.2 mmol) were added and the mixture was refluxed (external temperature 100 0C) until complete consumption of starting choropyrimidine (3 hours). The reaction mixture was cooled to room temperature and poured into water (200 ml) cooled to 10 0C. It was then extracted with EtOAc. The collected organic phases, containing large amount of colloid material and water, were washed with brine (200 ml). The aqueous phase was filtered over a gouch, and the solid material was washed with further EtOAc. The collected organic phases were dried overnight over Na2SO4, filtered and concentrated to give the crude material (7 g) which was purified (Biotage SpI over a 240 g Silica Analogix column, with a 25 g pre-column) to give the title compound D58 as yellow solid (1.8 g).UPLC (Acid GEN_QC_SS): rt = 0.58 minutes, peak observed: 197 (M+l) C11H8N4 requires 196.
Isopropylmagnesium chloride-LiCl (37.9 ml, 36.5 mmol) was added portion wise (in overall 10 min) to a solution of <strong>[717843-48-6]3-bromo-6-methyl-2-pyridinecarbonitrile</strong> (4 g, 20.30 mmol) in THF (150 ml) cooled to -70 0C (internal temperature). The reaction was kept to that temperature for 15 min. Then it was allowed to gently warm up to -40 0C in overall 1 hour. Then, it was cooled to -78 0C and zinc chloride (3.32 g, 24.36 mmol) was added. The resulting mixture was allowed to warm up to room temperature in 1 hour. Pd(Ph3P)4 (2.346 g, 2.030 mmol), 2-chloropyrimidine (3 g, 26.2 mmol) were added and the mixture was refluxed (external temperature 100 0C) until complete consumption of startingchloropyrimidine (3 hours). The reaction mixture was cooled to room temperature and poured into water (200 ml) cooled to 10 0C. It was then extracted with EtOAc. The collected organic phases, containing large amount of colloid material and water, were washed with brine (200 ml). The water phase was filtered over a gouch, and the solid material was washed with further EtOAc. The collected organic phases were dried overnight over Na2SO4, filtered and concentrated to give (7 g) the crude material which was purified (Biotage SpI over a 240 g Silica Anolgix column, with a 25 g pre-column) to give the title compound D8 as yellow solid (1.8 g). UPLC (Acid GEN QC SS): rt = 0.58 minutes, peak observed: 197 (M+l). C11H8N4 requires 196.
Isopropylmagnesium chloride-LiCl (37.9 ml, 36.5 mmol) was added portion wise (in overall 10 min) to a solution of <strong>[717843-48-6]3-bromo-6-methyl-2-pyridinecarbonitrile</strong> (4 g, 20.30 mmol) in THF (150 ml) cooled to -70 0C (internal temperature). The reaction was kept to that temperature for 15 min. Then it was allowed to gently warm up to -40 0C in overall 1 hour. Then, it was cooled to -78 0C and zinc chloride (3.32 g, 24.36 mmol) was added. The resulting mixture was allowed to warm up to room temperature in 1 hour. Pd(Ph3P)4 (2.346 g, 2.030 mmol), 2-chloropyrimidine (3 g, 26.2 mmol) were added and the mixture was refluxed (external temperature 100 0C) until complete consumption of startingchloropyrimidine (3 hours). The reaction mixture was cooled to room temperature and poured into water (200 ml) cooled to 10 0C. It was then extracted with EtOAc. The collected organic phases, containing large amount of colloid material and water, were washed with brine (200 ml). The water phase was filtered over a gouch, and the solid material was washed with further EtOAc. The collected organic phases were dried overnight over Na2SO4, filtered and concentrated to give (7 g) the crude material which was purified (Biotage SpI over a 240 g Silica Anolgix column, with a 25 g pre-column) to give the title compound DlO Nl 1358-28-1 as yellow solid (1.8 g). UPLC (Acid GEN_QC_SS): rt = 0.58 minutes, peak observed: 197 (M+l). C11HsN4 requires 196.
A) Isopropylmagnesium chloride-LiCl (37.9 ml, 36.5 mmol) was added portion wise (in overall 10 min) to a solution of <strong>[717843-48-6]3-bromo-6-methyl-2-pyridinecarbonitrile</strong> (4 g, 20.30 mmol) in THF (150 ml) cooled to -70 C (internal temperature). The reaction was kept to that temperature for 15 min. Then it was allowed to gently warm up to -40 C in overall 1 hour. Then, it was cooled to -78 C and zinc chloride (3.32 g, 24.36 mmol) was added. The resulting mixture was allowed to warm up to room temperature in 1 hour. Pd(Ph3P)4 (2.346 g, 2.030 mmol), 2-chloropyrimidine (3 g, 26.2 mmol) were added and the mixture was refluxed (external temperature 100 C) until complete consumption of startingchloropyrimidine (3 hours). The reaction mixture was cooled to room temperature and poured into water (200 ml) cooled to 10 C. It was then extracted with EtOAc (5 x 200 ml). The collected organic phases, containing large amount of colloid material and water, were washed with brine (200 ml). The water phase was filtered over a gouch, and the solid material was washed with further EtOAc (2 x 300ml). The collected organic phases were dried overnight over Na2S04, filtered and concentrated to give the crude material (7 g) which was purified (Biotage Spl over a 240 g Silica Analogix column, with a 25 g pre- column) to give the title compound D32 as yellow solid (1.8 g). UPLC (AcidGEN_QC_SS): rt = 0.58 minutes, peak observed: 197 (M+l). CnH8N4 requires 196.
A) Isopropylmagnesium chloride-LiCl (37.9 ml, 36.5 mmol) was added portion wise (in overall 10 min) to a solution of <strong>[717843-48-6]3-bromo-6-methyl-2-pyridinecarbonitrile</strong> (4 g, 20.30 mmol in THF (150 ml) cooled to -70 C (internal temperature). The reaction was kept to that temperature for 15 min. Then it was allowed to gently warm up to -40 C in overall 1 hour. Then, it was cooled to -78 C and zinc chloride (3.32 g, 24.36 mmol) was added. The resulting mixture was allowed to warm up to room temperature in 1 hour. Pd(Ph3P)4 (2.346 g, 2.030 mmol), 2-chloropyrimidine (3 g, 26.2 mmol) were added and the mixture was refluxed (external temperature 100 C) until complete consumption of startingchloropyrimidine (3 hours). The reaction mixture was cooled to room temperature and poured into water (200 ml) cooled to 10 C. It was then extracted with EtOAc (5 x 200mls). The collected organic phases, containing large amount of colloid material and water, were washed with brine (200 ml). The water phase was filtered over a gouch, and the solid material was washed with further EtOAc (2 x 300mls). The collected organic phases were dried overnight over Na2S04, filtered and concentrated to give (7 g) the crude material which was purified (Biotage Spl over a 240 g Silica Anolgix column, with a 25 g pre- column) to give the title compound D68 as yellow solid (1.8 g). UPLC (AcidGEN_QC_SS): rt = 0.58 minutes, peak observed: 197 (M+l). Cn¾N4 requires 196.
Isopropylmagnesium chloride-LiCl (37.9 ml, 36.5 mmol) was added portion wise (in overall 10 min) to a solution of <strong>[717843-48-6]3-bromo-6-methyl-2-pyridinecarbonitrile</strong> (4 g, 20.30 mmol) in THF (150 ml) cooled to -70 0C (internal temperature). The reaction was kept to that temperature for 15 min. Then it was allowed to gently warm up to -40 0C in overall 1 hour. Then, it was cooled to -78 0C and zinc chloride (3.32 g, 24.36 mmol) was added. The resulting mixture was allowed to warm up to room temperature in 1 hour. Pd(Ph3P)4 (2.346 g, 2.030 mmol), 2-chloropyrimidine (3 g, 26.2 mmol) were added and the mixture was refluxed (external temperature 100 0C) until complete consumption of starting chloropyrimidine (3 hours). The reaction mixture was cooled to room temperature and poured into water (200 ml) cooled to 10 0C. It was then extracted with EtOAc (5 x 200 mis). The collected organic phases, containing large amount of colloid material and water, were washed with brine (200 ml). The water phase was filtered over a gouch, and the solid material was washed with further EtOAc 2 x 300 mis). The collected organic phases were dried overnight over Na2SO4, filtered and concentrated to give (7 g) the crude material which was purified (Biotage SpI over a 240 g Silica Anolgix column, with a 25 g pre- column) to give the title compound D 18 as yellow solid (1.8 g). UPLC (Acid GEN_QC_SS): rt = 0.58 minutes, peak observed: 197 (M+l). CnH8N4 requires 196

  • 6
  • [ 717843-48-6 ]
  • [ 1268817-70-4 ]
  • 7
  • [ 717843-48-6 ]
  • [ 1268817-71-5 ]
  • 8
  • [ 717843-48-6 ]
  • [ 1268817-58-8 ]
  • 9
  • [ 717843-48-6 ]
  • [ 1268817-59-9 ]
  • 10
  • [ 717843-48-6 ]
  • [ 1268817-64-6 ]
  • 11
  • [ 717843-48-6 ]
  • [ 1268818-50-3 ]
  • 12
  • [ 717843-48-6 ]
  • [ 1268818-51-4 ]
  • 13
  • [ 717843-48-6 ]
  • [ 1268818-36-5 ]
  • 14
  • [ 717843-48-6 ]
  • [ 1268818-44-5 ]
  • 15
  • [ 288-36-8 ]
  • [ 717843-48-6 ]
  • [ 1620-75-3 ]
  • [ 1384199-29-4 ]
  • [ 1384199-28-3 ]
YieldReaction ConditionsOperation in experiment
22.24% With copper(I) trifluoromethanesulfonate benzene; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; caesium carbonate; In N,N-dimethyl-formamide; at 120℃; for 4h;Inert atmosphere; A solution of <strong>[717843-48-6]3-bromo-6-methylpyridine-2-carbonitrile</strong> (3 g, 15.23 mmol), lH-l,2,3-triazole (2.103 g, 30.5 mmol), (lR^^-^jV-dimethyl-l^-cyclohexanediamine (0.433 g, 3.05 mmol), cesium carbonate (9.92 g, 30.5 mmol) in dry DMF (30 ml) was degassed with argon bubbling for 5 minutes. Then bis(copper(I)trifluoromethanesulfonate)benzene complex (0.383 g, 0.761 mmol) was finally added and the resulting mixture was further de-gassed with argon bubbling for 30 seconds. Reaction mixture was heated at 120C for 4 hours. Reaction mixture was cooled down to room temperature and water (50 ml) was added. Mixture was taken up with EtOAc (100 ml). Emulsion formed, separation of phases was difficult, so further water 50 ml and EtOAc (50 ml) were added but separation still remained very difficult. Aqueous layer was back extracted with EtOAc (2x50 ml). Combined organic phases were washed with brine (30ml) and evaporated to dryness to get crude material (3.7 g) as thick brown oil that was purified over Si02 Biotage SNAP lOOg (eluting withCy/EtOAc 9/1 to 6/4). Evaporation of solvent afforded 3 fractions:6-methyl-2-pyridinecarbonitrile (0.4 g, 3.39 mmol, 22.24 % yield) as white solid;UPLC (IPQC): rt = 0.60 minutes peak observed: 119 (M+l);D45 6-methyl-3-(lH-l,2,3-triazol-l-yl)-2-pyridinecarbonitrile (0.68 g) as white solid UPLC (IPQC): rt = 0.58 minutes peak observed: 186 (M+l) C9H7N5 requires 185.1H NMR (400 MHz, CHLOROFORM-^ delta ppm 2.74 (s, 3 H) 7.62 (d, 1 H) 7.97 (d, 1 H) 8.22 (d, 1 H) 8.39 (d, 1 H)D46 6-methyl-3-(2H-l,2,3-triazol-2-yl)-2-pyridinecarbonitrile (1 g) as white solidUPLC (IPQC): rt = 0.74 minutes, peak observed: 186 (M+l) C9H7N5 requires 1851H NMR (400 MHz, CHLOROFORM-^ delta ppm 2.71 (s, 3 H) 7.54 (d, 1 H) 7.99 (s, 2 H) 8.34 (d, 1 H)
  • 16
  • [ 717843-48-6 ]
  • [ 1228430-59-8 ]
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  • [ 717843-48-6 ]
  • [ 1228188-16-6 ]
  • 19
  • [ 717843-48-6 ]
  • [ 1228188-17-7 ]
  • 20
  • [ 717843-48-6 ]
  • [ 1252905-76-2 ]
  • 21
  • [ 717843-48-6 ]
  • [ 1228430-57-6 ]
  • 22
  • [ 717843-48-6 ]
  • [ 1228430-58-7 ]
  • 23
  • [ 717843-48-6 ]
  • [ 1384199-17-0 ]
  • 24
  • [ 717843-48-6 ]
  • [ 1384199-22-7 ]
  • 25
  • [ 717843-48-6 ]
  • [ 1384199-23-8 ]
  • 26
  • [ 717843-48-6 ]
  • [ 1384199-24-9 ]
  • 27
  • [ 717843-48-6 ]
  • [ 1384199-25-0 ]
  • 28
  • [ 717843-48-6 ]
  • [ 1384261-51-1 ]
  • 29
  • [ 717843-48-6 ]
  • [ 1384261-52-2 ]
  • 30
  • [ 717843-48-6 ]
  • [ 1384261-68-0 ]
  • 31
  • [ 717843-48-6 ]
  • 3-bromo-6-methyl-2-pyridinecarboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With sodium hydroxide; In ethanol; at 90℃;Inert atmosphere; A mixture of 183 <strong>[717843-48-6]3-bromo-6-methylpicolinonitrile</strong> 17c (15 g, 76.1 mmol), 90 sodium hydroxide solution (4 N, 56 mL, 228 mmol) and 21 ethanol (150 mL) was heated to 90 C. and stirred overnight. The mixture was cooled to room temperature, acidified with hydrochloride solution and concentrated under reduced pressure to remove solvent. The residue was washed with dichloromethane to give the target 185 compound 3-bromo-6-methylpicolinic acid 17d (15.8 g, oil). Yield: 99%. MS m/z (ESI): 216/218[M+1]
69.3% With hydrogenchloride; at 110℃; (3) the 2 - bromo -6 - methyl -2 - cyano pyridine (25g, 127mmol) dissolved in the 1L in concentrated hydrochloric acid (HCl), mixture in 110 C stirring reaction under the condition of 2 days; removing the solvent to obtain crude product; the obtained crude product is dissolved in water, and addingNaHCO3, then filtered; the filtrate is ethyl acetate extraction, Na2SO4drying and vacuum concentrated to get the crude product 3 - bromo -6 - methyl -2 - picolinic acid; two product adds up the yield of 69.3%, about 19g.
With sodium hydroxide; In ethanol; at 90℃; for 48h;Sealed tube; Step A: 3-bromo-6-methylpicolinic acid. To <strong>[717843-48-6]3-bromo-6-methylpicolinonitrile</strong> (4 g, 20.3 mmol) in EtOH (40 mL) in a sealed tube was added aqueous 4M NaOH (15 mL). The reaction was heated at 90 C. for 24 h. Additional aqueous 4M NaOH was added and heating continued at 90 C. for 24 h. The reaction was cooled to rt, acidified to pH=3 with 1N HCl (aq), concentrated and used without further purification in subsequent steps. MS (ESI) mass calcd. for C7H6BrNO2, 216.0; m/z found 218 [M+H]+.
With water; sodium hydroxide; In ethanol; at 90℃; for 48h;Sealed tube; 10330] To <strong>[717843-48-6]3-bromo-6-methylpicolinonitrile</strong> (4 g, 20.3 mmol) in EtOH (40 mE) in a sealed tube was added aqueous 4M NaOH (15 mE). The reaction was heated at 90 C. for 24 h. Additional aqueous 4M NaOH was added and heating continued at 90 C. for 24 h. The reaction was cooled to it, acidified to pH=3 with iN HC1 (aq), concentrated and used without thrther purification in subsequent steps. MS (ESI) mass calcd. for C7H5BrNO2, 216.0; mlz found 218 [M+H].

  • 32
  • [ 717843-48-6 ]
  • [ 288-36-8 ]
  • 5-methyl-3-(2H-1,2,3-triazol-2-yl)picolinonitrile [ No CAS ]
  • 5-methyl-3-(1H-1,2,3-triazol-1-yl)picolinonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
35%; 27% With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 16h; Step A: 5-methyl-3-(2H-1,2,3-triazol-2-yl)picolinonitrile To 3-bromo-5-methylpicolinic acid (1.5 g, 7.6 mmol) in DMF (19 mL) was added K2CO3 (1.2 g, 8.4 mmol) and 2H-1,2,3-triazole (440 muL, 7.6 mmol). The mixture was heated to 100 C. for 16 h, cooled to room temperature and extracted with EtOAc (2*). The combined organics were dried (Na2SO4) and concentrated. Purification via silica gel chromatography (5-60% EtOAc in hexanes) gave the title compound (490 mg, 35%) 1H NMR (500 MHz, Chloroform-d) 8.58-8.53 (m, 1H), 8.29-8.24 (m, 1H), 7.98 (s, 2H), 2.54 (s, 3H) and 5-methyl-3-(1H-1,2,3-triazol-1-yl)picolinonitrile (387 mg, 27%).
  • 33
  • [ 717843-48-6 ]
  • [ 288-36-8 ]
  • [ 1384199-29-4 ]
YieldReaction ConditionsOperation in experiment
48% With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 36h; Step A: 6-methyl-3-(2H-1,2,3-triazol-2-yl)picolinonitrile To 3-bromo-5-methylpicolinonitrile (2.2 g, 11 mmol) in DMF (28 mL) was added K2CO3 (1.7 g, 12 mmol) and 2H-1,2,3-triazole (650 muL, 11 mmol). The mixture was heated to 100 C. for 36 h, cooled to rt and extracted with EtOAc. The combined organics were dried (Na2SO4) and concentrated. Purification via silica gel chromatography (10-100% EtOAc in hexanes) gave the title compound (1 g, 48%).
48% With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 36h; Step A: 6-methyl-3-(2H-1,2,3-triazol-2-yl)picolinonitrile. To 3-bromo-5-methylpicolinonitrile (2.2 g, 11 mmol) in DMF (28 mL) was added K2CO3 (1.7 g, 12 mmol) and 2H-1,2,3-triazole (650 muL, 11 mmol). The mixture was heated to 100 C. for 36 h, cooled to rt and extracted with EtOAc. The combined organics were dried (Na2SO4) and concentrated. Purification via silica gel chromatography (10-100% EtOAc in hexanes) gave the title compound (1 g, 48%).
48% With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 36h; j0294] To 3-bromo-6-methylpicolinonitrile (2.2 g, ii mmol) in DMF (28 mE) was added K2C03 (i .7 g, i2 mmol) and 2H-i,2,3-triazole (650 pL, ii mmol). The mixture was heated to iOO C. for 36 h, cooled to rt and extracted with EtOAc. The combined organics were dried (Na2504) and concentrated. Purification via silica gel chromatography (i 0- i 00% EtOAc in hexanes) gave the title compound (i g, 48%).
  • 34
  • [ 717843-48-6 ]
  • (sodium 5-methyl-3-(2H-1,2,3-triazol-2-yl)picolinate) [ No CAS ]
  • 35
  • [ 717843-48-6 ]
  • (6-methyl-3-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)((1S,4R,6R)-6-((5-(trifluoromethyl)pyridin-2-yl)oxy)-2-azabicyclo[2,2,1]heptan-2-yl)methanone [ No CAS ]
  • 36
  • [ 717843-48-6 ]
  • methyl 3-bromo-6-methyl-2-pyridinecarboxylate [ No CAS ]
  • 37
  • [ 717843-48-6 ]
  • methyl 6-methyl-3-(oxazol-2-yl)picolinate [ No CAS ]
  • 38
  • [ 717843-48-6 ]
  • 6-methyl-3-(oxazol-2-yl)picolinic acid [ No CAS ]
  • 39
  • [ 717843-48-6 ]
  • methyl 3,6'-dimethyl-[2,3'-bipyridine]-2'-carboxylate [ No CAS ]
  • 40
  • [ 717843-48-6 ]
  • (+/-)-(6-methyl-3-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)(2-((pyridazin-3-yloxy)methyl)-7-azabicyclo[2.2.1]heptan-7-yl)methanone [ No CAS ]
  • 41
  • [ 717843-48-6 ]
  • 3-(dimethylamino)-6-methylpicolinic acid [ No CAS ]
  • 42
  • [ 717843-48-6 ]
  • [ 124-40-3 ]
  • 3-(dimethylamino)-6-methylpicolinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% at 140℃; for 2h;Microwave irradiation; 10570] A mixture of <strong>[717843-48-6]3-bromo-6-methylpicolinonitrile</strong> (1 g, 5 mmol) and dimethylamine (2 mE) were heated in a microwave reactor for 2 hat 140 C. The mixture was then concentrated and purified via silica gel chromatography (0-5% MeOH in DCM) to give the title compound (249 g, 27%). MS (ESI) mass calcd. for C9H,3N30, 179.1; mlz found 180.0 [M+H].
  • 44
  • [ 717843-48-6 ]
  • 3-bromo-6-methyl-2-pyridinemethanol [ No CAS ]
  • 45
  • [ 717843-48-6 ]
  • 3-bromo-6-methyl-2-pyridinecarboxaldehyde [ No CAS ]
  • 46
  • [ 717843-48-6 ]
  • [ 372963-49-0 ]
  • 5,6'-dimethyl-[2,3'-bipyridine]-2'-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 120℃; for 0.5h; To a mixture of <strong>[717843-48-6]3-bromo-6-methylpicolinonitrile</strong> (1.0 eq), (5-methylpyridin-2-yl)boronic acid (1.3 eq) and K2CO3 (3.0 eq) in dioxane/H2O (4:1) was added Pd(PPh3)4 (10mol %). The mixture was degassed and then heated for 30 min at 120C in a microwave reactor. The completion of the reaction was monitored by analytical HPLC. When complete, the reaction mixture was cooled to RT and diluted with EtOAc and washed with H2O and the layers were separated. The aqueous layer was extracted with EtOAc (2x). The combined organic layers were concentrated to provide the crude which was purified by column chromatography on silica gel to obtain the desired product. ESI-MS (m/z): 210.09 [M+1]+.
  • 47
  • [ 717843-48-6 ]
  • [ 372963-49-0 ]
  • 5,6'-dimethyl-[2,3'-bipyridine]-2'-carboxylic acid [ No CAS ]
  • 48
  • [ 717843-48-6 ]
  • ethyl 2-(3-bromo-6-methylpyridine-2-carbonyl)4-pentenoate [ No CAS ]
  • 49
  • [ 717843-48-6 ]
  • ethyl 2-(3-isopropenyl-6-methylpyridine-2-carbonyl)-4-pentenoate [ No CAS ]
  • 50
  • [ 717843-48-6 ]
  • 2,5-dimethyl-5-ene-9-oxo-cyclohepta[b]pyridine-8-carboxylic acid ethyl ester [ No CAS ]
  • 51
  • [ 717843-48-6 ]
  • ethyl 2,5-dimethyl-5-ene-9-hydroxy-cyclohepta[b]pyridine-8-carboxylate [ No CAS ]
  • 52
  • [ 717843-48-6 ]
  • C15H17NO2 [ No CAS ]
  • 53
  • [ 717843-48-6 ]
  • methyl 2,5-dimethyl-5,8-diene-cyclohepta[b]pyridine-8-carboxylate [ No CAS ]
  • 54
  • [ 717843-48-6 ]
  • C14H19NO2 [ No CAS ]
  • C14H19NO2 [ No CAS ]
  • 55
  • [ 717843-48-6 ]
  • [ 6148-64-7 ]
  • ethyl 3-(3-bromo-6-methylpyridine)-3-carbonylpropionate [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% c. Under vacuum, heat the mass ratio of 40:60 zinc chloride containing crystal water to 7.2 g (32.5 mmol) to melt.Water, under the protection of nitrogen, sequentially added 75 ml of 1,2-dichloroethane, Compound 3 was <strong>[717843-48-6]3-bromo-6-methyl-2-cyanopyridine</strong> 5.5 g(27.9 mmol), potassium monoethyl malonate 11 g (64.7 mmol) and diisopropylethylamine 1.5 ml (9.1 mmol), and stirred at refluxAfter 12 hours, after the system was cooled to room temperature, 20 mL of 6N hydrochloric acid was added and the mixture was refluxed for another hour. The organic phase was separated and the aqueous phase was replaced with dichloromethan.Extract three times with alkane, combine the organic phases and dry over anhydrous magnesium sulfate, remove the organic solvent, and purify to obtain compound 4 as 3-(3-Bromo-6-methylpyridine)-3-carbonylpropanoic acid ethyl ester, yield 82%, 6.6 g;
  • 56
  • [ 717843-48-6 ]
  • [ 38330-80-2 ]
  • methyl 3-(3-bromo-6-methylpyridin-2-yl)-3-oxopropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% Under vacuum,Crystal water with a mass ratio of 40:60:8 g (36.1 mmol) of zinc chloride is heated to melt and remove water.Under nitrogen protection, 75 ml of 1,2-dichloroethane was added in sequence.Compound 3 is <strong>[717843-48-6]3-bromo-6-methyl-2-cyanopyridine</strong> 5.5g(27.9mmol),13 g (77 mmol) of monomethyl malonate potassium salt and 1.8 ml (11.0 mmol) of diisopropylethylamine were stirred and refluxed for 16 hours.After the system was cooled to room temperature, 20 ml of 6N hydrochloric acid was added.Returning again for 1 hour, separating the organic phase,The aqueous phase was extracted 3 times with dichloromethane.The organic phases were combined and dried over anhydrous magnesium sulfate.Remove organic solvent, purify,The compound 4 is obtained as methyl 3-(3-bromo-6-methylpyridine)-3-carbonylpropanoate, the yield is 82%, 6.6 g;
  • 57
  • [ 717843-48-6 ]
  • C14H19NO2 [ No CAS ]
  • 58
  • [ 717843-48-6 ]
  • [ 41447-00-1 ]
  • 59
  • [ 717843-48-6 ]
  • 2-((5S,8S)-2,5-dimethyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-8-yl)propan-2-ol [ No CAS ]
  • 2-[(5R,8R)-2,5-dimethyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-8-yl]propan-2-ol [ No CAS ]
  • 60
  • [ 717843-48-6 ]
  • methyl 2-(3-bromo-6-methylpicolinoyl)pent-4-enoate [ No CAS ]
  • 61
  • [ 717843-48-6 ]
  • methyl 2-(3-isopropenyl-6-methylpyridine-2-formyl)-4-pentenoate [ No CAS ]
  • 62
  • [ 717843-48-6 ]
  • methyl 2,5-dimethyl-5-ene-9-oxo-cyclohepta[b]pyridine-8-carboxylate [ No CAS ]
  • 63
  • [ 717843-48-6 ]
  • methyl 2,5-dimethyl-5-ene-9-hydroxy-cyclohepta[b]pyridine-8-carboxylate [ No CAS ]
  • 64
  • 2,7-diazaspiro[4.4]-nonane-2-carboxylic acid tert-butyl ester [ No CAS ]
  • [ 717843-48-6 ]
  • C19H26N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; XPhos; In toluene; at 90℃; for 16h;Inert atmosphere; Sealed tube; General procedure: Pd2(dba)3 (37.6 mg, 0.039 mmol) and BINAP (CAS: 98327-87-8; 38.3 mg, 0.06 mmol) were added to a stirred mixture of tert-butyl 2,7-diazaspiro[4.4]nonane-2- carboxylate (CAS: 236406-49-8; 170 mg, 0.75 mmol), 5-bromopyrimidine (137 mg, 0.86 mmol) and cesium carbonate (411 mg, 1.26 mmol) in toluene at rt while a N2 stream was bubbled though the mixture. Then the reaction mixture was stirred at 90 C into a sealed tube and under N2 atmosphere for 16 h. The mixture was cooled to rt and them it was filtered through diatomaceous earth and the diatomaceous earth pad was washed with EtOAc. The combined organic filtrates were evaporated in vacuo to yield crude intermediate 42 (262 mg, 66% yield, 58% pure) as an orange syrup. The compound was used in the next reaction step without further purification.
  • 65
  • [ 717843-48-6 ]
  • [ 1228187-94-7 ]
  • 66
  • [ 717843-48-6 ]
  • [ 1228187-95-8 ]
  • 67
  • [ 3430-13-5 ]
  • [ 7677-24-9 ]
  • [ 717843-48-6 ]
YieldReaction ConditionsOperation in experiment
66% To a solution of 5-bromo-2-methylpyridine (1.00 g, 5.81 mmol) in CHCb (15 mL) was added mCPBA (1.10 g, 6.39 mmol). The reaction mixture was stirred at room temperature for 4 h, then washed with saturated aqueous Na2C03 solution (50 mL) and extracted with DCM (2 x 40 mL). The organic layer was separated, dried over anhydrous Na2S04 and concentrated in vacuo. The resulting pale yellow solid was redissolved in acetonitrile (28 mL) at room temperature, then trimethylsilyl cyanide (2.24 mL, 17.9 mmol) and trimethylamine (1.10 mL, 13.4 mmol) were added. The reaction mixture was stirred at l00C for 16 h, then cooled to room temperature and concentrated in vacuo. The crude residue was purified by column chromatography (silica, 100-200 mesh, 20% EtOAc in hexanes) to afford the title compound (0.7 g, 66%) as a pale yellow solid. 6n (400 MHz, CDCb) 2.58 (s, 3H), 7.26 (d, J 8.8 Hz, 1H), 7.88 (d, J 8.4 Hz, 1H).
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