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Chemical Structure| 62226-17-9 Chemical Structure| 62226-17-9

Structure of 62226-17-9

Chemical Structure| 62226-17-9

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Product Details of [ 62226-17-9 ]

CAS No. :62226-17-9
Formula : C7H4ClNS
M.W : 169.63
SMILES Code : ClC1=C(C=CS2)C2=NC=C1
MDL No. :MFCD11858513
InChI Key :QWAORBHZRDAYQE-UHFFFAOYSA-N
Pubchem ID :598066

Safety of [ 62226-17-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 62226-17-9 ]

* 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 [ 62226-17-9 ]

[ 62226-17-9 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 65075-96-9 ]
  • [ 62226-17-9 ]
  • 2
  • [ 62226-17-9 ]
  • [ 25557-54-4 ]
YieldReaction ConditionsOperation in experiment
99% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 3.25h; To a solution of 4-chlorothieno[2,3- Z>]pyridine (450 mg, 2.65 mmol, 1 eq.) in DCM (14.7 mL) was added 3-chloroperoxybenzoic acid (1.78 g, 7.95 mmol, 3 eq.) over 15 minutes. After three hours, the reaction was quenched with 10% NaS2C>3 solution and washed with 10% K2CO3. The aqueous layer was back extracted with 3: 1 CHCI3/IPA solution. The organic layers were combined, dried (MgS04), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 500 mg (99%) of the title compound. XH NMR (400 MHz, DMSO-c) delta 8.42 (d, J = 6.6 Hz, 1H), 8.06 (d, J = 5.7 Hz, 1H), 7.65 (d, J = 6.6 Hz, 1H), 7.54 (d, J= 5.7 Hz, 1H); ES- MS [M+l]+: 186.4.
  • 3
  • [ 110651-85-9 ]
  • [ 62226-18-0 ]
  • [ 62226-17-9 ]
  • 4
  • [ 110651-85-9 ]
  • [ 62226-17-9 ]
  • 5
  • [ 62226-17-9 ]
  • [ 124-41-4 ]
  • [ 99429-85-3 ]
  • 6
  • [ 62226-17-9 ]
  • [ 99429-89-7 ]
  • 7
  • [ 59713-52-9 ]
  • [ 62226-17-9 ]
  • 8
  • [ 55503-31-6 ]
  • [ 62226-17-9 ]
  • 9
  • [ 55503-32-7 ]
  • [ 62226-17-9 ]
  • 10
  • [ 62226-17-9 ]
  • trans-4-(dimethylamino)cyclohexan-1-ol [ No CAS ]
  • [ 1388893-18-2 ]
YieldReaction ConditionsOperation in experiment
6% Example 130. N,N-dimethyl-4-[thieno[2,3-b]pyridin-4-yloxy]cyclohexan-l-amine.Molecular Weight: 169.63 Molecular Weight: 276.41Into a 50-mL round-bottom flask, was placed a solution of 4-(dimethylamino)cyclohexan- l -ol (127 mg, 0.89 mmol, 1.50 equiv) in N,N-dimethylformamide (15 mL). This was followed by the addition of sodium hydride (71 mg, 1.77 mmol, 3.00 equiv, 60%). The resulting solution was stirred for 30 minutes at 80C in an oil bath. <strong>[62226-17-9]4-chlorothieno[2,3-b]pyridine</strong> ( 100 mg, 0.59 mmol, 1.00 equiv) was added to the mixture. The resulting solution was stirred for 3 h at 120C in an oil bath. The reaction was then quenched by the addition of 10 mL of ethanol. The resulting mixture was concentrated under vacuum. The residue was purified on a silica gel column with dichloromethane/methanol (10: 1 ). The resulting product (50 mg) was further purified by Prep- HPLC with the following conditions: Column, SunFire Prep C 18, 19* 150mm 5um; mobile phase, CH3CN and water with 0.05% NH4HCO3 (3.0% water with 0.05% NH4HCO3 up to 3.0% in 1 min, up to 4.7.0% in l3 min,up to 100.0% in 2 min); Detector, uv 254/220nm. This resulted in 9.6 mg (6%) of N,N-dimethyl-4-[thieno[2,3-b]pyridin-4-yloxy]cyclohexan-l-amine as a white solid.MS: (ES, m/z): 277.10 [M+H] + NMR (300 MHz, CD3OD, ppm): 61.49- 1.69 (m, 4H), 2.06 (d, J= 12.3 Hz , 2H), 2.34(m, 9H), 4.60(m, 1 H), 7.01 (d, J= 5.8 Hz , 1H), 7.38(d, J=6.0 Hz , 1 H), 7.52(d, J= 6.3 Hz , 1 H), 8.36(d, J= 5.8 Hz , 1 H).
  • 11
  • [ 64-18-6 ]
  • [ 62226-17-9 ]
  • [ 167298-52-4 ]
  • 1-N,1-N-dimethyl-4-N-(thieno[2,3-b]pyridin-4-yl)cyclohexane-1,4-diamine formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% Example 129. l-N,l-N-dimethyl-4-N-[thieno[2,3-b]pyridin-4-yl]cyclohexane-l,4-diamine.Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of <strong>[62226-17-9]4-chlorothieno[2,3-b]pyridine</strong> (commercially available, 100 mg, 0.59 mmol, 1.00 equiv) in toluene ( 15 mL), l -N, l-N-dimethylcyclohexane-l ,4-diamine (126 mg, 0.89 mmol, 1.50 equiv), Pd2(dba)3 chloroform (30 mg, 0.03 mmol, 0.05 equiv), XantPhos (34 mg, 0.06 mmol, 0.10 equiv), t-BuONa(l 13mg, 1.18 mmol, 2.00 equiv). The resulting solution was stirred overnight at 100C in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (6: 1). The crude product (50 mg) was purified by Prep-HPLC with the following conditions: Column, SunFire Prep C18, 19* 150mm 5um; mobile phase, CH3CN and water with 0.05%HCOOH (10.0% water with 0.05%HCOOH up to 50.0% in 10 min, up to 100.0% in 2 min down to 10.0% in 2 min); Detector, uv 254/220nm.This resulted in 23.4 mg (14%) of l -N, l-N-dimethyl-4-N- [thieno[2,3-b]pyridin-4-yl]cyclohexane- l ,4-diamine as yellow semi-solid. MS: (ES, m/z): 276.10 [M- 1.56HCOOH+H]+ .'H NMR- (300 MHz, CDC13, ppm): 51.20- 1.47 (m, 2H), 1.60- 1.72 (m, 2H), 2.21 -2.38 (m, 4H), 2.69(s, 6H), 3.00-3.13 (m, 1 H)3.71 (s, 1 H),4.72 (m, 1 H), 6.38(d, J= 5.7 Hz, 1H), 7.19 (d, J=6.0 Hz, 1 H), 7.30 (d, J = 6.0 Hz, 1 H), 8.25 (d, J = 5.4 Etazeta, Iota Eta), 8.48 (s, 1.56H,), 9.01 -9.15(br, 1 H).
  • 12
  • [ 64-18-6 ]
  • [ 62226-17-9 ]
  • [ 1228947-14-5 ]
  • 4-[4-(thieno[2,3-b]pyridin-4-yloxy)cyclohexyl]morpholine formate [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% 131. 4-(4-[thieno[2,3-b]pyridin-4-yloxy]cyclohexyl)morpholine.Page 221 of 4072009184-0008 Molecular Weight: 169.63 Molecular Weight: 379.191Into a 50-mL round-bottom flask, was placed a solution of 4-(morpholin-4-yl)cyclohexan-l-ol (164 mg, 0.89 mmol, 1.50 equiv) in N,N-dimethylformamide (15 mL), sodium hydride (47 mg, 1.96 mmol, 2.00 equiv). The resulting mixture was stirred at 80 C for 30 minutes. Then 4- chlorothieno[2,3-b]pyridine (100 mg, 0.59 mmol, 1.00 equiv) was added to the mixture. The resulting solution was stirred for 4 h at 120C in an oil bath. The reaction was then quenched by the addition of 5 mL of water. The resulting solution was extracted with 3x30 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3x 15 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (10: 1). The crude product (120 mg) was purified by Prep-HPLC with the following conditions: Column, SunFire Prep C18, 19* 150mm 5um; mobile phase, CH3CN and water with 0.05% HCOOH (10.0% water with 0.05% HCOOH up to 50.0% in 10 min, up to 100.0% in 2 min, down to 10.0% in 2 min); Detector, uv 254/220nm. This resulted in 72.2 mg (32%) of 4-(4-[thieno[2,3- b]pyridin-4-yloxy]cyclohexyl)morpholine as a white semi-solid. MS:(ES,/n/z): 319.10 [M+H]+ NMR (400 MHz, O20, ppm): 51.53-1.71 (m, 4H), 2.19-2.33 (dd, Jl= 29.7 Hz , J2= 9.3Hz, 4H), 3.24-3.30(m, 3H),3. 1(m, 2H), 4.07(s, 2H), 4.60(m, 1H), 6.98(d, J= 4.5 Hz , 1H), 7.37(d, J= 4.5Hz , 1H), 7.52(d, J= 4.5Hz , 1H), 8.33(d, J= 4.5Hz , 1H).
  • 13
  • [ 62226-17-9 ]
  • [ 86344-90-3 ]
  • 14
  • [ 62226-17-9 ]
  • 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thieno[2,3-b]pyridine-6-carbonitrile [ No CAS ]
  • 15
  • [ 62226-17-9 ]
  • 4-(4-(2-methyloxazol-4-yl)benzyl)thieno[2,3-b]pyridine-6-carbonitrile [ No CAS ]
  • 16
  • [ 62226-17-9 ]
  • 4-(4-(2-methyloxazol-4-yl)benzyl)thieno[2,3-b]pyridine-6-carboxylic acid [ No CAS ]
  • 17
  • [ 62226-17-9 ]
  • 4-[[4-(2-methyloxazol-4-yl)phenyl]methyl]-N-tetrahydropyran-4-ylthieno[2,3-b]pyridine-6-carboxamide [ No CAS ]
  • 18
  • [ 62226-17-9 ]
  • 4-hydrazinylthieno[2,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
88.2% With hydrazine; at 100℃; A solution of <strong>[62226-17-9]4-chlorothieno[2,3-b]pyridine</strong> (600 mg, 3.54 mmol) in hydrazine (5 mL, 98%) was stirred at 100 C. overnight. The solid was filtered and washed by 2 mL water. The solid was collected and dried to afford 126a (550 mg, 88.2% yield) as a white solid. LCMS (ESI) m/z M+1: 165.9.
  • 19
  • [ 62226-17-9 ]
  • ethyl 1-(thieno[2,3-b]pyridin-4-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate [ No CAS ]
  • 20
  • [ 62226-17-9 ]
  • 1-(thieno[2,3-b]pyridin-4-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid [ No CAS ]
  • 21
  • [ 62226-17-9 ]
  • N-(5-cyano-6-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)-1-(thieno[2,3-b]pyridin-4-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxamide [ No CAS ]
  • 22
  • [ 62226-17-9 ]
  • 2-bromo-4-chlorothieno[2,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% To a 100 ml three-necked flask was added 4-chlorothiophene [2,3-b]pyridine (5 g, 0.029 mol), THF (20ml), nitrogen protection,n-BuLi (18 ml, 0.044 mol) was added dropwise at -78 C. After the completion of the dropwise addition, the reaction was carried out at -78 C for 30 min, and then bromine (9.28 g, 0.058 mol) was added dropwise.After the addition is completed, the temperature is naturally raised to room temperature at -78 C.After the TLC monitoring reaction was completed, a saturated sodium sulfite solution was added.The mixture was extracted with EtOAc.The concentrated solvent was purified by silica gel column chromatography to afford intermediate int8 (5.811 g, yield 81%).
  • 23
  • [ 62226-17-9 ]
  • 3-bromo-4-chlorothieno[2,3-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With bromine; acetic acid; at 20℃; for 18h; To a 100 ml three-necked flask was added 4-chlorothiophene [2,3-b]pyridine (5 g, 0.029 mol), Acetic acid (20 ml), bromine (9.28 g, 0.058 mol) was added dropwise at room temperature. After the completion of the dropwise addition, the reaction was carried out for 18 hours, and after the TLC monitoring reaction was completed, a saturated sodium sulfite solution was added.The mixture was extracted with EtOAc. The concentrated solvent was purified by silica gel column chromatography to afford Intermediate int9 (6.319 g, yield 87%).
  • 24
  • [ 62226-17-9 ]
  • 2,3-dibromo-4-chlorothieno[2,3-b]pyridine [ No CAS ]
  • 25
  • [ 62226-17-9 ]
  • [ 68-12-2 ]
  • 4-chlorothieno[2,3-b]pyridine-2-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
86 mg To a solution of <strong>[62226-17-9]4-chloro-thieno[2,3-b]pyridine</strong> (107 mg; 0.62 mmol) in THF (8 mL) was added lithium diisopropylamide (0.078 mL; 0.62 mmol) at -78 C. The mixture was stirred for 1 h and DMF (0.051 mL; 0.65 mmol) was added. After stirring for 1 h at -78 C, water (1 mL) was cautiously added and the mixture was concentrated. The residue was purified by column chromatography (silica gel; PE : EA; 10:1 ; v/v) to afford <strong>[62226-17-9]4-chlorothieno[2,3-b]pyridine</strong>-2-carbaldehyde (86 mg) as a yellow solid. (1025) MS m/z (+ESI): 198.0, 200.0 [M+H]+. (1026) 'H-NMR (400 MHz, DMSO-i) delta ppm: 10.19 (s, 1H), 8.72 (d, J= 5.2 Hz, 1H), 8.55 (s, 1H), 7.77 (d, J= 5.2 Hz, 1H).
 

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