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[ CAS No. 4347-31-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 4347-31-3
Chemical Structure| 4347-31-3
Structure of 4347-31-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4347-31-3 ]

CAS No. :4347-31-3 MDL No. :MFCD01075678
Formula : C5H5BO3S Boiling Point : -
Linear Structure Formula :- InChI Key :BBENFHSYKBYWJX-UHFFFAOYSA-N
M.W : 155.97 Pubchem ID :2773426
Synonyms :

Calculated chemistry of [ 4347-31-3 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 39.53
TPSA : 85.77 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.3
Log Po/w (WLOGP) : -0.76
Log Po/w (MLOGP) : -1.44
Log Po/w (SILICOS-IT) : 0.16
Consensus Log Po/w : -0.35

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.23
Solubility : 9.1 mg/ml ; 0.0583 mol/l
Class : Very soluble
Log S (Ali) : -1.66
Solubility : 3.38 mg/ml ; 0.0217 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.49
Solubility : 50.2 mg/ml ; 0.322 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.11

Safety of [ 4347-31-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4347-31-3 ]

* 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 [ 4347-31-3 ]

[ 4347-31-3 ] Synthesis Path-Downstream   1~85

  • 2
  • [ 4347-31-3 ]
  • thieno[2,3-<i>d</i>][1,2,6]oxazaborinin-1-ol [ No CAS ]
  • 3
  • [ 4347-31-3 ]
  • 2<i>H</i>-thieno[3,2-<i>d</i>][1,2,3]diazaborinin-1-ol [ No CAS ]
  • 5
  • [ 4347-31-3 ]
  • [ 60-34-4 ]
  • [ 17303-89-8 ]
  • 7
  • [ 109-04-6 ]
  • [ 4347-31-3 ]
  • [ 150711-16-3 ]
  • 8
  • [ 6298-19-7 ]
  • [ 4347-31-3 ]
  • [ 62506-44-9 ]
  • 9
  • [ 39856-58-1 ]
  • [ 4347-31-3 ]
  • [ 62506-44-9 ]
  • 10
  • [ 13534-99-1 ]
  • [ 4347-31-3 ]
  • thieno<2,3-c><1,8>naphthyridine [ No CAS ]
  • 11
  • [ 13534-98-0 ]
  • [ 4347-31-3 ]
  • [ 62506-41-6 ]
  • 12
  • [ 13535-03-0 ]
  • [ 4347-31-3 ]
  • [ 62506-41-6 ]
  • 13
  • [ 614-76-6 ]
  • [ 4347-31-3 ]
  • [ 233-04-5 ]
  • 14
  • [ 4347-31-3 ]
  • [ 148873-30-7 ]
  • [ 148873-31-8 ]
  • 15
  • [ 4347-31-3 ]
  • [ 155444-28-3 ]
  • thieno<2,3-c><1,8>naphthyridine [ No CAS ]
  • 16
  • [ 141-97-9 ]
  • [ 4347-31-3 ]
  • [ 57-13-6 ]
  • N2C4H3O(CH3)(COOC2H5)(C4H2SB(OH)2) [ No CAS ]
  • 17
  • [ 90-11-9 ]
  • [ 4347-31-3 ]
  • 3-(1-naphthyl)thiophene-2-carboxaldehyde [ No CAS ]
  • 18
  • [ 89682-86-0 ]
  • [ 4347-31-3 ]
  • [ 874142-97-9 ]
  • 19
  • [ 4347-31-3 ]
  • [ 350584-53-1 ]
  • [ 842167-24-2 ]
  • 20
  • [ 1000199-03-0 ]
  • [ 4347-31-3 ]
  • 3-{3-[3-amino-1-(4-methoxyphenyl)-1H-isoindol-1-yl]phenyl}thiophene-2-carbaldehyde acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
4% With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; ethanol; water; at 130℃; for 0.25h;Microwave irradiation; Example 48; 3-{3-[3-Amino-l-(4-methoxyphenyl)-lJH-isoindol-l-yl]phenyl}thiophene-2- carbaldehyde; 1.5 acetate (Scheme No.8, B)l-(3-Bromophenyl)-l-(4-methoxyphenyl)-lH-isoindol-3-amine (0.079 g, 0.2 mmol) (Scheme No.8, A), (2-formyl-3-thienyl)boronic acid (0.047 g, 0.3 mmol), [1,1'- bis(diphenylphosphmo)ferrocene]palladium(II) chloride dichloromethane adduct (0.016 g, 0.02 mmol), potassium carbonate (0.083 g, 0.6 mmol) and solvent (3 mL of a mixture of dimethoxy ethane, water and ethanol in a ratio of 6:3:1) was irradiated under an argon atmosphere in a microwave at 130 0C for 15 min. When cooled to ambient temperature the <n="86"/>mixture was filtered and dimethyl sulfoxide (1.0 mL) was added. The solution was concentrated in vacuo and purified by preparative HPLC to give 0.003 g (4 percent yield) of the title compound. 1HNMR (DMSO-J6) delta 9.68 (s, 1 H), 8.15 (d, J= 5.02 Hz, 1 H)5 7.79 (dd, J= 5.52, 3.01 Hz, 1 H), 7.73 (dd, J= 5.52, 2.76 Hz, 1 H), 7.68 - 7.53 (m, 1 H), 7.50 - 7.38 (m, 5 H), 7.33 (d, J= 5.02 Hz, 1 H), 7.26 (d, J= 8.78 Hz, 2 H), 6.83 (d, J= 8.78 Hz, 2 H), 3.71 (s, 3 H), 1.91 (s, 3 H); MS (AP) m/z 425 [M+lf.
  • 21
  • [ 4347-31-3 ]
  • [ 500169-22-2 ]
  • C20H17NO3S2 [ No CAS ]
  • 22
  • [ 4347-31-3 ]
  • [ 500169-21-1 ]
  • C20H17NO3S2 [ No CAS ]
  • 23
  • [ 4347-31-3 ]
  • [ 119671-47-5 ]
  • C14H13NO4S [ No CAS ]
  • 24
  • [ 832727-21-6 ]
  • [ 4347-31-3 ]
  • [ 936833-14-6 ]
  • 25
  • [ 4347-31-3 ]
  • 2-(4-ethoxyphenoxy)-5-[2-(1-hydroxytridec-2-ynyl)-3-thienyl]benzenesulfonic acid [ No CAS ]
  • 26
  • [ 4347-31-3 ]
  • 2-(2-methoxy-vinyl)-3-naphthalen-1-yl-thiophene [ No CAS ]
  • 27
  • [ 4347-31-3 ]
  • 7-[ (2, 4-dichloro-5-methoxyphenyl) amino]-2-{2-[ (4-methylpiperazin-1-yl) methyl] thien-3-yl} thieno [3,2-b] pyridine-6-carbonitrile [ No CAS ]
  • 28
  • [ 4347-31-3 ]
  • 4-{3-(2-Hydroxymethyl-thiophen-3-yl)-2-[2-((R)-2-methyl-pyrrolidin-1-yl)-ethyl]-benzofuran-5-yl}-benzonitrile [ No CAS ]
  • 29
  • [ 4347-31-3 ]
  • methyl (2Z)-3-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thien-2-yl]acrylate [ No CAS ]
  • 30
  • [ 4347-31-3 ]
  • [ 700846-24-8 ]
  • 31
  • [ 4347-31-3 ]
  • methyl (2E)-3-{3-[(1RS,2SR,4RS,5SR,6RS)-2,4-dimethyl-3-oxo-8-oxabicyclo[3.2.1]oct-6-yl]thien-2-yl}acrylate [ No CAS ]
  • 32
  • [ 4347-31-3 ]
  • C17H20O4S [ No CAS ]
  • 33
  • [ 4347-31-3 ]
  • C17H19(2)HO4S [ No CAS ]
  • 34
  • [ 4347-31-3 ]
  • [ 10341-88-5 ]
  • 35
  • [ 4347-31-3 ]
  • 3-phenyl-thiophene-2-carbonyl chloride [ No CAS ]
  • 36
  • [ 4347-31-3 ]
  • 3-phenylthiophene-2-carbonyl azide [ No CAS ]
  • 37
  • [ 4347-31-3 ]
  • [ 148873-35-2 ]
  • 38
  • [ 4347-31-3 ]
  • pyrido<1,2-b>thieno<3,2-d>pyridazin-6-ium perchlorate [ No CAS ]
  • 39
  • [ 4347-31-3 ]
  • [ 17303-93-4 ]
  • 40
  • [ 4347-31-3 ]
  • [ 916673-46-6 ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate; In isopropyl alcohol; at 0℃; for 3h; Step 1. (3- (3-AMINO-4-NITROPHENYL) THIOPHEN-2-YL) METHANOL (90); [0272] A suspension of the aldehyde 89 (500 mg, 3.21 MMOL) and sodium borohydride (121 mg, 3.21 mmol) in isopropanol (5 ml) was stirred at 0°C during 3 h. The excess of hydride was quenched with acetone, and the solvent was evaporated. A suspension of the resulting boronic acid (or any other boronic acid), 5-bromo-2-nitroaniline (2) (697 mg, 3.21 mmol) (scheme 1, Example 1) POT (305 mg, 1.00 MMOL), PD (PPH3) 4 (241 mg, 0.209 MMOL) and K2C03 (1.33 g, 9.63 MMOL) in DME (12 ML) and water (4 ml) was stirred during 16 h at 80°C. The solvent was evaporated; ethyl acetate was added and washed with saturated solution of NACI. The organic layer was dried over MGS04, filtered and concentrated. After purification by flash chromatography on silica gel (eluent 40percent EtOAc in Hexanes), 605 mg (75percent) of compound 90 was obtained as a orange OIL. H NMR: (400 MHz, DMSO) 8 (ppm): 7.98 (d, J = 9.0 Hz, 1H), 7.52 (d, J = 5.3 Hz, 1H), 7.44 (s, 2H), 7.15 (d, J = 5.3 Hz, 1H), 7.02 (d, J = 1.8 Hz, 1H), 6.73 (DD, J = 9. 0, 2.0 Hz, 1H), 5.72 (t, J = 5. 4 Hz, 1H), 4.70 (d, J = 5.5 Hz, 2H).
  • 41
  • [ 841290-03-7 ]
  • [ 4347-31-3 ]
  • N4-(3,4-ethylenedioxyphenyl)-5-fluoro-2-(2-formylthien-3-yl)-N4-methyl-4-pyrimidineamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; ethanol; water; at 155℃; for 0.183333h;Microwave irradiation; A mixture of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-N4-methyl-4-pyrimidineamine (50 mg, 0.17 mmol), (2-formylthien-3-yl)boronic acid (40 mg, 0.26mmole), dichlorobis(triphenylphosphine)palladium(II) (25 mg, 0.035 mmol), and 1.5 NNa2CO3 (0.128 mL, 0.187 mmol) in 0.50 mL solvent (DME:H2O:EtOH, 7:3:2; v/v/v) wasadded to a sealed microwave tube. The reaction mixture was heated in microwave at 155°C for 660 seconds. After cooling to room temperature, the reaction mixture was filteredthrough Celite and the filter cake washed with methanol. Concentration in vacuo gavethe crude product, which was purified by chromatography (silica gel, eluted with 1percentethyl acetate in hexanes ramped up to 20percent ethyl acetate in hexanes). .H NMR (CDC13):6 10.74 (s, 1H), 8.01 (d, J= 5.4 Hz, 1H), 7.77 (d, J= 5.4 Hz, 1H), 7.55 (dd, J= 1.2 and 5.4Hz, 1H), 6.79 (d, J= 8.7 Hz, 1H), 6.68 (d, J= 2.1 Hz, 1H), 6.63 (dd, J= 2.4 and 8.4 Hz,1H), 4.21 (s, 4H), 3.43 (s, 3H); LCMS: purity: 91percent; MS (m/e): 372 (MH+).
  • 42
  • [ 482627-80-5 ]
  • [ 4347-31-3 ]
  • [ 482627-68-9 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 49 1,4-Bis[5-(2-formyl-3-thienyl)-2-pyridyl]hexahydro-1,4-diazepine Following the procedure of Example 1, the title compound was obtained as a pale yellow amorphous powder (71.0 mg, yield: 74percent) from 1,4-bis(5-bromo-2-pyridyl)hexahydro-1,4-diazepine (82.0 mg, 0.200 mmol) synthesised in Reference Example 1 and <strong>[4347-31-3]2-formylthiophene-3-boronic acid</strong> (69.0 mg, 0.44 mmol). 1H-NMR (DMSO-d6,120° C.) delta: 2.02 (tt, J=6.0, 6.0 Hz, 2 H), 3.71 (dd, J=6.0, 6.0 Hz, 4 H), 3.94 (s, 4 H), 6.77 (d, J=8.7 Hz, 2 H), 7.27 (d, J=4.8 Hz, 2 H), 7.65 (dd, J=2.6, 8.7 Hz, 2 H), 7.97 (dd, J=1.2, 4.8 Hz, 2 H), 8.25 (d, J=2.6 Hz, 2 H), 9.78 (d, J=1.2 Hz, 2 H).
YieldReaction ConditionsOperation in experiment
c) Preparation of 2-formyl-3-thiopheneboronic acid Butyl lithium (7.9 ml of 2.5M solution in hexanes ex Aldrich) was slowly added to a solution of the dioxolane from (b) (4.28 parts, 0.018M) in dry diethylether with stirring at -70° C. under a nitrogen blanket. After stirring for 15 mins butyl borate (6 mls ex Aldrich) dissolved in ethylether (20 ml) was slowly added at -70° C. The reactants were stirred for a further 4 hours at -700C and then warmed to 20° C. 25 ml N hydrochloric acid was added and the reactants stirred for 1 hour at 20° C. The ether layer was then separated and extracted with N aqueous sodium carbonate solution (3*10 ml). This aqueous carbonate solution was slowly acidified whereupon the product separated and was filtered and dried. Yield=0.89 parts. Elemental Analysis Found 36.6percent C, 3.0percent H, 19.6percent STheory 38.5percent c, 3.2percent H, 20.5percent S
c. 2-Formylthiophen-3-boronic Acid (4) A 1.1 N solution of n-butyllithium in hexane (28 ml). was added dropwise (10 mins) to a solution of 2-(3-bromo-2-thienyl)-1,3-dioxalane (3) (6.6 g, 28.1 mmol) in anhydrous ether (30 ml) at -70° C. After stirring for 10 mins, butyl borate (9.1 ml, 33.7 mmol) in anhydrous ether (20 ml) was added in a single portion. The reaction mixture was stirred for 4 hrs at -70° C. and then left to return to room temperature. 1 N hydrochloric acid (20 ml) was added, and the mixture was left for 1 hr with stirring. The aqueous phase was extracted with ether and the combined ether phases were washed with a solution of sodium bicarbonate, dried (Na2SO4), and evaporated under reduced pressure to give the intermediate (4) (2.2 g, 14.1 mmol, 50percent yield) as a brown solid. 1H-NMR (CDCl3) ae 7.0 (brs, 2H, OH), 7.77 (d J=5.1 Hz, 1H, th-H), 7.85 (d J=5.2, 1H, th-H), 9.75 (s, 1H, CHO).
YieldReaction ConditionsOperation in experiment
EXAMPLE 55 3-(4-(2-Formylthienyl)phenyl)-3-[2-(4-({2-pridinylamino}methyl) phenoxy)-4primidinyl]propanoic acid Using derivatised resin (Intermediate 142) and 2-formylthiophene-3-boronic acid yielded the title compound. HPLC-MS Retention time 2.19 min MH+ 537
  • 45
  • [ 774213-79-5 ]
  • [ 4347-31-3 ]
  • [ 886042-36-0 ]
YieldReaction ConditionsOperation in experiment
84% With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; water; for 0.75h;Heating / reflux; Step 1: Methyl l-(2'tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-(2-formyl-3-thienyl)-lH-indole-6-carboxylate; Methyl 2-bromo-l-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-lH-indole-6-carboxylate (prepared as described in Example 1, Step 1) and (2-formyl-3-thienyl) boronic acid (1.5 eq) were dissolved in dioxane (0.07 M) and 2M aqueous Na2CO3 (6 eq) was added. The solution was degassed by bubbling argon, Pd(PPh3)2Cl2 (0.2 eq) was added, and the reaction mixture was refluxed for 45 min; after cooling EtOAc was added and the solution washed with water and brine, dried over Na2SO4 and concentrated. The title compound was isolated by chromatography (PE/EtOAc 9:1). Yield (84percent); MS (ES+) m/z 504 (M+Na)+.
  • 46
  • [ 591-50-4 ]
  • [ 4347-31-3 ]
  • [ 26170-85-4 ]
  • 47
  • [ 578-57-4 ]
  • [ 4347-31-3 ]
  • [ 666841-73-2 ]
  • 48
  • [ 2372-88-5 ]
  • [ 4347-31-3 ]
  • [ 17303-89-8 ]
  • 49
  • [ 4347-31-3 ]
  • [ 302-01-2 ]
  • [ 4347-35-7 ]
  • 50
  • [ 584-12-3 ]
  • [ 4347-31-3 ]
  • [ 1040531-72-3 ]
  • 51
  • [ 847551-49-9 ]
  • [ 4347-31-3 ]
  • [ 1138320-63-4 ]
  • [ 1138320-62-3 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 1h; EXAMPLE 3 (Entry 3, Table A and Entry 4, Table A); 2-(2-C-methyl-beta-D-ribofuranosyl)-2,6-dihydro-7H-8-thia-2,3,5,6-tetraazabenzo [CDlcyclopenta[eta]azulen-7-one and 2-(2-C-methyl-beta-D-ribofuranosyl)-6,7-dihydro-2H-8-thia- 2,3,5,6-tetraazabenzorCDl cvclopenta|eta1azulene <n="22"/>; Pd(Ph3P)4 (0.1 eq) was added to a solution of 5-iodo-7-(2-C-methyl-beta-D-ribofuranosyl)-7H- pyrrolo[2,3-d]pyrimidin-4-amine (1.0 eq), (2-formylphenyl)boronic acid (1.5 eq) and sodium carbonate (2M aqueous solution, 3 eq) in dioxane and the resulting mixture was heated at 1000C for Ih. The solution was allowed to cool to RT and then filtered through a pad of celite. The filter cake was washed with methanol and the filtrate was concentrated under reduced pressure. The dark residue obtained was purified by preparative RP-etaPLC eluting with MeCN/water containing 0.1percentTFA to give 2-(2-C-methyl-beta-D-ribofuranosyl)-2,6-dihydro-7H-8-thia-2,3,5,6- tetraazabenzo[CD]cyclopenta[eta]azulen-7-one as first eluting product and 2-(2-C-methyl-beta-D- ribofuranosyl)-6,7-dihydro-2H-8-thia-2,3,5,6-tetraazabenzo[CD]cyclopenta[H]azulene as second eluting product.2-(2-C-methyl-beta-D-ribofuranosyl)-2,6-dihydro-7H-8-thia-2,3,5,6-tetraazabenzo [CD]cyclopenta[eta]azulen-7-one: 1H NMR (600 MHz, DMSO-d6) delta 11.07 (s, IH), 8.39 (s, IH), 8.20 (s, IH), 8.02 (d, J4.6, IH), 7.74 (d, J4.6, IH), 6.19 (s, IH), 5.31-5.16 (m, 3H), 4.02 (m, IH), 3.94 (m, IH), 3.89 (m, IH), 3.76 (m, IH) 0.79 (s, 3H); MS (ES+) Ci7Hi6N4O5S requires: 388, found: 389 (M+H+).2-(2-C-methyl-beta-D-ribofuranosyl)-6,7-dihydro-2H-8-thia-2,3,5,6-tetraazabenzo[CD] cyclopenta[eta]azulene: 1H NMR (600 MHz, D2O/CD3CN) delta 8.24 (s, IH), 7.96 (s, IH), 7.37 (d, J 5.3, IH), 7.30 (d, J5.3, IH), 6.26 (s, IH), 4.69 (s, 2H), 4.10 (d, J 8.8, IH), 4.03-3.96 (m, 2H), 3.85-3.82 (m, IH), 0.86 (s, 3H). MS (ES+) Ci7Hi8N4O4S requires: 374, found: 375 (M+H+).
  • 52
  • [ 40473-07-2 ]
  • [ 4347-31-3 ]
  • [ 1177369-16-2 ]
YieldReaction ConditionsOperation in experiment
88% With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In ethanol; water; toluene; at 90℃; To a 500 mL flask was added <strong>[4347-31-3]2-formylthiophene-3-boronic acid</strong> (3OA, 5.00 g, 32.1 mmol, 1.0 eq.), 2-bromo-6-methoxypyridine (3OB, 6.03 g, 32.1 mmol, 1.0 eq.), toluene (100 mL), EtOH (100 mL), aqueous sodium carbonate (2N, 32 ml, 64 mmol, 2.0 eq.), and Pd(dppf)Cl2 (1.17 g, 1.6 mmol, 0.05 eq.). The reaction was stirred overnight at 90 0C. The reaction was cooled and saturated aqueous NaCl (100 mL) was added and the mixture was stirred for 20 min. The reaction mixture was extracted with EtOAc (2 x 100 mL) and the resulting organic layers were combined and passed through a Celite pad to remove residual Pd. The organic phases were washed with a succession Of H2O (100 mL) and saturated aqueous NaCl (100 mL) and then dried over anhydrous Na2SO4, filtered, and concentrated to give a bubbly brown solid that was used in the next step without further purification (6.2 g, 88percent). ESI-MS: m/z 220.2 (M+H)+.
  • 53
  • [ 420797-72-4 ]
  • [ 4347-31-3 ]
  • [ 420797-94-0 ]
  • 54
  • [ 1229168-51-7 ]
  • [ 4347-31-3 ]
  • [ 1229168-48-2 ]
  • 55
  • [ 35450-36-3 ]
  • [ 4347-31-3 ]
  • [ 1283600-45-2 ]
  • 56
  • [ 4347-31-3 ]
  • 5-(1-hydroxy-4-methylpentan-2-yl)-8-methoxy-6-oxo-N-(2,4,4-trimethylpentan-2-yl)-5,6-dihydro-4H-benzo[ c]thieno[3,2-e]azepine-4-carboxamide [ No CAS ]
  • 5-(1-hydroxy-4-methylpentan-2-yl)-8-methoxy-6-oxo-N-(2,4,4-trimethylpentan-2-yl)-5,6-dihydro-4H-benzo[ c]thieno[3,2-e]azepine-4-carboxamide [ No CAS ]
  • 57
  • [ 4347-31-3 ]
  • [ 953062-84-5 ]
  • 58
  • C13H20BNO3S [ No CAS ]
  • [ 4347-31-3 ]
  • 59
  • [ 4347-31-3 ]
  • [ 84459-33-6 ]
  • [ 1392144-29-4 ]
  • 60
  • [ 4347-31-3 ]
  • [ 84459-33-6 ]
  • [ 1392143-93-9 ]
  • 61
  • [ 4347-31-3 ]
  • [ 6630-33-7 ]
  • [ 1392144-28-3 ]
  • 62
  • [ 4347-31-3 ]
  • [ 6630-33-7 ]
  • [ 1392143-92-8 ]
  • 63
  • [ 847551-49-9 ]
  • [ 4347-31-3 ]
  • [ 1396441-39-6 ]
  • 64
  • [ 7321-27-9 ]
  • [ 4347-31-3 ]
  • [ 1301205-59-3 ]
YieldReaction ConditionsOperation in experiment
49% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 24h;Inert atmosphere; Reflux; In a four-necked 300 mL round bottomed flask, 2-bromoanthracene (6.3 g, 25 mmol), (2-formylthiophene-3-yl)boronic acid (5.0 g, 32 mmol, 1.3 eq.) and tetrakis(triphenylphosphine)palladium(0) (1.0 g, 0.87 mmol, 3 mol percent) were placed. After the inside of the flask was replaced with argon gas, dimethoxyethane (75 mL) and a 2M aqueous solution of sodium carbonate (35 mL, 70 mmol, 2.8 eq.) was added thereto, and the resulting mixture was heated under reflux for 1 day. After completion of the reaction, toluene and water were added. An organic phase was extracted with toluene, and dried over magnesium sulfate. The resulting crude product was purified by column chromatography, whereby intermediate A1 was obtained (3.5 g, yield 49percent).
  • 65
  • [ 7321-27-9 ]
  • [ 4347-31-3 ]
  • C21H16OS [ No CAS ]
  • C21H16OS [ No CAS ]
  • 66
  • 3-bromo-5-(2-pyridyl)-1-(3-pyridyl)-1,2-dihydropyridin-2-one [ No CAS ]
  • [ 4347-31-3 ]
  • [ 380919-24-4 ]
  • 67
  • [ 25187-00-2 ]
  • [ 4347-31-3 ]
  • C25H20N2O3S2 [ No CAS ]
  • 69
  • (1-bromonaphthalen-2-yl)(phenyl)methanone [ No CAS ]
  • [ 4347-31-3 ]
  • C29H22N2O3S2 [ No CAS ]
  • 70
  • (1-bromonaphthalen-2-yl)(phenyl)methanone [ No CAS ]
  • [ 4347-31-3 ]
  • [ 1433030-78-4 ]
  • 72
  • [ 26137-10-0 ]
  • [ 4347-31-3 ]
  • C23H18N2O3S3 [ No CAS ]
  • 74
  • [ 1350883-09-8 ]
  • [ 4347-31-3 ]
  • [ 1426667-98-2 ]
YieldReaction ConditionsOperation in experiment
22% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In N,N-dimethyl-formamide; at 80℃;Inert atmosphere; Step 1:To a solution of methyl 4-chloropyrrolo[l,2-f][l,2,4]triazin-2-ylcarbamate (17d)(0.52 g, 2.295 mmol) and <strong>[4347-31-3]2-formylthiophen-3-ylboronic acid</strong> (39a) (0.537 g, 3.44 mmol) in DMF (20 mL) was degassed with nitrogen gas for 15 min followed by addition of sodium carbonate (2 M in water, 4.02 mL, 8.03 mmol) under continuous follow of nitrogen.Palladium(II)bis(triphenylphosphine) dichloride (322 mg, 0.459 mmol) was added to the reaction mixture under nitrogen atmosphere. The reaction was stirred at 80 °C overnight, cooled to room temperature and quenched with water (40 mL). The reaction mixture was extracted with ethyl acetate (2 x 25 mL). The organic layers were combined washed with water (25 mL), brine (25 mL), dried, filtered and concentrated in vacuum to dryness. The residue obtained was purified by flash column chromatography (silica gel, 12 g eluting with 0-100percent ethyl acetate in hexane) to afford methyl 4-(2-formylthiophen-3-yl)pyrrolo[l,2- f][l,2,4]triazin-2-ylcarbamate (39b) (0.15 g, 22 percent yield) as light yellow solid. 1H NMR (300 MHz, DMSO-de) ? 10.51 - 10.42 (m, 2H), 8.27 (dd, J = 5.1, 1.2 Hz, 1H), 8.11 (dd, J = 2.5, 1.4 Hz, 1H), 7.94 (d, J = 5.1 Hz, 1H), 7.11 (dd, J = 4.7, 1.4 Hz, 1H), 7.04 (dd, J = 4.7, 2.5 Hz, 1H), 3.70 (s, 3H); MS (ES+) 303.0 (M+l); (ES-) 336.8 (M+Cl). Step 2:To a solution of methyl 4-(2-formylthiophen-3-yl)pyrrolo[l,2-f][l,2,4]triazin-2- ylcarbamate (39b) (1.5 g, 4.96 mmol) in acetonitrile (12 mL), t-BuOH (84 mL) was added sodium dihydrogenphosphate (1.191 g, 9.92 mmol) in water (6 mL) over a period of 5 min followed by 2-methylbut-2-ene (5.26 mL, 49.6 mmol). The reaction was cooled in an ice- water bath and then a solution of sodium chlorite (2.244 g, 24.81 mmol) in water (6 mL) was added dropwise over a period of 5 min. After stirring for 1.5 h, the reaction mixture diluted with water and extracted with ethyl acetate (3 x 60 mL). The combined organic layers were dried over MgSC^, filtered and concentrated in vacuum to dryness. The residue obtained was triturated with water and the solid obtained was collected by filtration, dried under vacuo to give 3-(2-(methoxycarbonylamino)pyrrolo[l,2-f][l,2,4]triazin-4- yl)thiophene-2-carboxylic acid (39c) (825 mg, 52 percent yield) as light yellow solid, which was used as such for the next step. 1H NMR (300 MHz, DMSO-d6) ? 13.26 (s, 1H), 10.39 (s, 1H), 8.08 - 7.98 (m, 2H), 7.41 (d, J= 5.1 Hz, 1H), 6.90 (dd, J= 4.6, 2.5 Hz, 1H), 6.57 (dd, J= 4.6, 1.4 Hz, 1H), 3.67 (s, 3H); MS (ES+) 319.0 (M+l), 340.9 (M+Na). Step 3:Diphenyl phosphorazidate (0.982 mL, 4.56 mmol) was added to a solution of 3-(2- (methoxycarbonylamino)pyrrolo[l,2-f][l,2,4]triazin-4-yl)thiophene-2-carboxylic acid (39c) (0.725 g, 2.278 mmol) and triethylamine (0.813 mL, 5.83 mmol) in tert-BuOH (25 mL). The mixture was stirred at 100 °C for 4 h and concentrated in vacuum to remove tert- butanol. To the residue was added water and ethylacetate. (1 : 1, 50 mL). The ethylacetate layer was separated, dried, filtered and concentrated in vacuum. The residue obtained was purified by flash column chromatography (silica gel 25 g, eluting with 0-100percent ethyl acetate in hexane) to furnish 2-tertbutoxycarbonylamino-3-(2-((methoxycarbonyl)amino)pyrrolo[2,l-f][l,2,4]triazin-4-yl)Thiophene (39d) (0.16 g, 18 percent> yield) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) ? 12.21 (s, 1H), 10.58 (s, 1H), 7.93 (dd, J= 2.5, 1.3 Hz, 1H), 7.83 (d, J= 6.0 Hz, 1H), 7.35 (dd, J= 4.9, 1.4 Hz, 1H), 7.14 (dd, J= 6.0, 0.8 Hz, 1H), 6.95 (dd, J= 4.7, 2.5 Hz, 1H), 3.73 (s, 3H), 1.53 (s, 9H); MS (ES+) 390.3 (M+l); (ES-) 388.1 (M-l).
  • 75
  • [ 1214996-37-8 ]
  • [ 4347-31-3 ]
  • [ 1435483-37-6 ]
YieldReaction ConditionsOperation in experiment
80% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In N,N-dimethyl-formamide; at 90℃; for 3h;Inert atmosphere; General procedure: General procedure for the synthesis of compounds 4a-d, 5a-c, 12, 17.1a,b,e,f, 17.2a,e, 23a,b, and 28 as exemplified 4a A solution of compound 2a (1.85 mmol, 760 mg) and Na2CO3 (5.55 mmol, 2 M) in DMF (10 mL) was degassed with nitrogen for 15 min. Thereafter 2-formyl phenylboronic acid (2.04 mmol, 280 mg) and Pd(PPh3)4 (0.09 mmol, 10 mg) were added to the reaction mixture under nitrogen atmosphere. The reaction mixture was stirred at 90 °C for 3 h. After completion, the reaction mass was diluted with water (50 mL) and extracted with EtOAc (3*25 mL). The organic layers were pooled, washed with brine dried over Na2SO4, and concentrated under reduced pressure to furnish a residue. Column chromatography of the residue over silica gel (hexanes/EtOAc, 85:15, v/v) afforded pure 4a as a white solid (69percent, 496 mg).
  • 76
  • [ 4347-31-3 ]
  • C25H24O2S [ No CAS ]
  • 77
  • [ 4347-31-3 ]
  • C20H16OS [ No CAS ]
  • 78
  • [ 100-39-0 ]
  • [ 4347-31-3 ]
  • 3-Benzylthiophene-2-carbaldehyde [ No CAS ]
  • 79
  • N-(1-(2-bromophenyl)-2-cyanoallyl)benzamide [ No CAS ]
  • [ 4347-31-3 ]
  • [ 67-63-0 ]
  • N-(5-cyano-4-hydroxy-5-(isopropoxymethyl)-5,6-dihydro-4H-benzo[3,4]cyclohepta[1,2-b]thiophen-6-yl)benzamide [ No CAS ]
  • 80
  • [ 64-17-5 ]
  • N-(1-(2-bromophenyl)-2-cyanoallyl)benzamide [ No CAS ]
  • [ 4347-31-3 ]
  • N-(5-cyano-4-hydroxy-5-(ethoxymethyl)-5,6-dihydro-4H-benzo[3,4]cyclohepta[1,2-b]thiophen-6-yl)benzamide [ No CAS ]
  • 81
  • [ 4347-31-3 ]
  • [ 159898-15-4 ]
  • 7H-indolo[3,2,1-ij]thieno[2,3-c][1,5]naphthyridin-7-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% General procedure: In a microwave vial, 1-bromo-9H-carbazole (1; 150 mg, 0.61mmol) or 1-bromo-9H-beta-carboline (2; 150 mg, 0.61 mmol), tetrakis(triphenylphosphine)palladium(0) (79 mg, 0.068 mmol), and the appropriate aryl- or heteroarylboronic acid (0.68 mmol) were suspended in a deoxygenated mixture of 1,2-dimethoxyethane (DME) and EtOH (3:2, 5 mL) under a nitrogen atmosphere. The tube was sealed and the mixture was stirred at r.t. for 10 min, then deoxygenated 2 M aq Na2CO3 (1 mL) was added. The mixture was kept undera nitrogen atmosphere and heated in the sealed vial under microwave irradiation (150 W, 90 °C, 15 min). After cooling to r.t., H2O(50 mL) was added, and the mixture was extracted with EtOAc(3 × 30 mL). The combined organic layers were dried over Na2SO4 and the solvents evaporated. Purification was accomplished by FCC using appropriate eluent mixtures outlined below.
  • 82
  • [ 16807-11-7 ]
  • [ 4347-31-3 ]
  • 7H-thieno[3′,2′:4,5]pyrido[3,2,1-jk]carbazol-7-one [ No CAS ]
  • 7H-thieno[3′,2′:4,5]pyrido[3,2,1-jk]carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% General procedure: In a microwave vial, 1-bromo-9H-carbazole (1; 150 mg, 0.61mmol) or 1-bromo-9H-beta-carboline (2; 150 mg, 0.61 mmol), tetrakis(triphenylphosphine)palladium(0) (79 mg, 0.068 mmol), and the appropriate aryl- or heteroarylboronic acid (0.68 mmol) were suspended in a deoxygenated mixture of 1,2-dimethoxyethane (DME) and EtOH (3:2, 5 mL) under a nitrogen atmosphere. The tube was sealed and the mixture was stirred at r.t. for 10 min, then deoxygenated 2 M aq Na2CO3 (1 mL) was added. The mixture was kept undera nitrogen atmosphere and heated in the sealed vial under microwave irradiation (150 W, 90 °C, 15 min). After cooling to r.t., H2O(50 mL) was added, and the mixture was extracted with EtOAc(3 × 30 mL). The combined organic layers were dried over Na2SO4 and the solvents evaporated. Purification was accomplished by FCC using appropriate eluent mixtures outlined below.
  • 83
  • ethyl 2-(benzamido(2-bromophenyl)methyl)acrylate [ No CAS ]
  • [ 4347-31-3 ]
  • [ 1611486-36-2 ]
  • 84
  • ethyl 2-(benzamido(2-bromophenyl)methyl)acrylate [ No CAS ]
  • [ 4347-31-3 ]
  • [ 1611486-21-5 ]
YieldReaction ConditionsOperation in experiment
82% General procedure: 4.2. General procedure for the synthesis of 3aA-3jA, 3aB-aE, 3bE as exemplified for 3aA: A suspension of 1a (0.20 g, 0.59 mmol), 2-formylphenylboronic acid 2A (0.09 g, 0.65 mmol), 2(M) aq Na2CO3 (0.13 g, 1.18 mmol) in dioxane (3 mL) was degassed under N2 for 15 min. Then a weighed amount of Pd(PPh3)4 (0.03 g, 0.03 mmol) was added to it and the reaction mixture was transferred to an oil bath and heated at 80 °C until all the starting materials were consumed. The excess 2-propanol was evaporated under reduced pressure and the crude mixture was worked up with EtOAc (3*10 mL). Thereafter the combined organic layer was washed with brine solution, dried over anhydrous Na2SO4, and evaporated under reduced pressure to yield the crude product as brown oil, which after chromatographic purification [silica gel, hexane/EtOAc (80:20)] yielded the pure 3aA (0.18 g, 79percent) as a white solid.
  • 85
  • N-(1-(2-bromophenyl)-2-cyanoallyl)benzamide [ No CAS ]
  • [ 4347-31-3 ]
  • [ 1611486-35-1 ]
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