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[ CAS No. 156635-90-4 ] {[proInfo.proName]}

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Chemical Structure| 156635-90-4
Chemical Structure| 156635-90-4
Structure of 156635-90-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 156635-90-4 ]

CAS No. :156635-90-4 MDL No. :MFCD09038417
Formula : C14H15BO4 Boiling Point : -
Linear Structure Formula :- InChI Key :UCYGEGISTWJFFA-UHFFFAOYSA-N
M.W : 258.08 Pubchem ID :15218755
Synonyms :

Calculated chemistry of [ 156635-90-4 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.14
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 73.74
TPSA : 58.92 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.26
Log Po/w (WLOGP) : 0.8
Log Po/w (MLOGP) : 1.22
Log Po/w (SILICOS-IT) : 0.8
Consensus Log Po/w : 1.02

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.0
Solubility : 0.257 mg/ml ; 0.000997 mol/l
Class : Soluble
Log S (Ali) : -3.13
Solubility : 0.19 mg/ml ; 0.000735 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.08
Solubility : 0.0214 mg/ml ; 0.0000828 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.16

Safety of [ 156635-90-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 156635-90-4 ]

* 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 [ 156635-90-4 ]

[ 156635-90-4 ] Synthesis Path-Downstream   1~27

  • 1
  • [ 156635-90-4 ]
  • [ 1309567-73-4 ]
  • [ 76513-69-4 ]
  • [ 1309567-89-2 ]
  • [ 1309567-88-1 ]
  • 2
  • [ 156635-90-4 ]
  • [ 1309567-86-9 ]
  • [ 1309567-88-1 ]
  • 3
  • [ 156635-90-4 ]
  • [ 1309567-74-5 ]
  • 4
  • [ 156635-90-4 ]
  • C16H17NO5 [ No CAS ]
  • 5
  • [ 156635-90-4 ]
  • C15H15NO5 [ No CAS ]
  • 6
  • [ 156635-90-4 ]
  • C14H13NO5 [ No CAS ]
  • 7
  • [ 1227077-01-1 ]
  • [ 156635-90-4 ]
  • [ 1446137-62-7 ]
  • 8
  • methyl 4-(((2-((4-bromobenzyl)oxy)phenethyl)(5-methoxy-5-oxopentyl)amino)methyl)benzoate [ No CAS ]
  • [ 156635-90-4 ]
  • [ 1476774-63-6 ]
  • 9
  • [ 156635-90-4 ]
  • [ 1320213-39-5 ]
  • C26H21NO3 [ No CAS ]
  • 10
  • [ 156635-90-4 ]
  • [ 1320213-39-5 ]
  • C31H33NO4Si [ No CAS ]
  • 11
  • [ 156635-90-4 ]
  • (S)-ethyl 2-(5-bromo-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate [ No CAS ]
  • (S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-5-(4-((4-methoxybenzyl)oxy)phenyl)-2,6-dimethylpyridin-3-yl)acetic acid [ No CAS ]
  • 12
  • [ 156635-90-4 ]
  • (S)-ethyl 2-(5-bromo-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate [ No CAS ]
  • (S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)5-(4-((4-methoxybenzyl)oxy)phenyl)-2,6-dimethylpyridin-3-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
64.1% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In N,N-dimethyl-formamide; at 110℃; for 2h; 10096] A mixture of (S)-ethyl 2-(5-bromo-4-(4,4-dimeth- ylpiperidin- 1 -yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy) acetate (0.0454 g, 0.100 mmol), (4-((4-methoxybenzyl)oxy) phenyl)boronic acid (0.039 g, 0.lSOmmol)and2MNa2CO3 (0.125 ml, 0.249 mmol) in DMF 92 mE) was degassed for 10 mm. Then, Pd(Ph3P)4 (0.012 g, 9.97 pmol) was added, degassed for 5 mm and placed in a oil bath pre-heated to 110C. Afier 2 h, cooled and purified by pre-HPEC to afford(S)-ethyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1 -yl)5-(4-((4-methoxybenzyl)oxy)phenyl)-2,6-dimethylpyridin-3-yl)acetate (0.0376 g, 0.064 mmol, 64.1% yield) as whitesolid. ?H NMR (500 MHz, CDC13) oe 7.40-7.44 (m, 2H),7.15-7.18 (m, 1H), 7.04-7.09 (m, 3H), 6.94-6.98 (m, 2H),6.05 (br. s., 1H), 5.05-5.11 (m, 2H), 4.27 (qd, J=7.1, 10.8 Hz,1H), 4.18 (qd, J=7.1, 10.7 Hz, 1H), 3.86 (s, 3H), 3.19 (bt s.,1H), 2.87 (bt s., 1H), 2.63 (bt s., 3H), 2.24 (bt s., 4H), 2.05(br.s., 1H), 1.26 (t, J=7.1 Hz, 3H), 1.20 (s, 9H), 0.90 (m, 3H),0.66 (bt s., 3H). 4H of piperidine were not resolved. ECMS(M+H)=589.4.
  • 13
  • [ 156635-90-4 ]
  • C11H9BrN4O [ No CAS ]
  • C25H22N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In 1,4-dioxane; water; at 80℃; for 17h;Schlenk technique; Inert atmosphere; Example Al 13: Preparation of Co. 112 In a Schlenk tube, a mixture of 4 (700 mg, 2.39 mmol), 4-(4'- methoxybenzyloxy)phenylboronic acid (1.85 g, 7.16 mmol), K3PO4 (2.03 g, 9.55 mmol) in 1,4-dioxane (10.5 mL) and H20 (3.5 mL) was carefully purged with N2. PCy3 (134 mg, 0.478 mmol) and Pd(OAc)2 (54 mg, 239 mumol) were added and the r.m. was purged again with N2. The Schlenk tube was then sealed and the r.m. was stirred for 17 h at 80C. The crude material was dissolved in water (17mL) and filtered on glass frit. The grey precipitate was washed with water (2x 20mL) and with Et20 (2x 40mL). The solid was collected to afford 1.40 g which was purified by prep. LC (irregular SiOH 15- 40 mupiiota, 50g Merck, mobile phase gradient: from DCM 100% to DCM 85%, MeOH 15%)). The pure fractions were collected and solvent evaporated to give 700 mg of Co. 112, white solid (69%).
  • 14
  • [ 156635-90-4 ]
  • 4-bromo-5-(3,5-difluorobenzyl)-2-fluorobenzonitrile [ No CAS ]
  • 5-[(3,5-difluorophenyl)methyl]-2-fluoro-4-[4-[(4-methoxyphenyl)methoxy]phenyl]benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; water; at 100℃; for 1.5h;Sealed tube; Inert atmosphere; Microwave irradiation; To a microwave vial were added 4-bromo-5-(3,5-difluorobenzyl)-2- fluorobenzonitrile (0.14 mmol, 46 mg), cesium carbonate (0.7 mmol, 228 mg), [4-[(4-methoxyphenyl)methoxy]phenyl] boronic acid (0.154 mmol, 40 mg) and tetrakis(triphenylphosphine)palladium (0.014 mmol, 16 mg). The vial was sealed under Argon atmosphere. A degassed solution of dioxane/water 3:1 was added to the vial (1.5 ml) and the mixture was heated at 100C for 90 minutes in a microwave reactor. The crude is diluted with DCM, washed with water, brine, dried over sodium sulfate, filtered andevaporated to dryness.The crude was purified by flash column chromatography with eluent Hexane/AcOEt 9:1 affording the title compound as a white solid (48 mg, 68%).1H NMR (400 MHz, CDC13) oe 7.39 (dd, J= 13.7, 7.6 Hz, 3H), 7.21 - 7.05 (m, 3H),7.00 (d, J= 8.8 Hz, 2H), 6.94 (d, J= 8.7 Hz, 2H), 6.73 - 6.55 (m, 1H), 6.42 (d, J 6.0 Hz,2H), 5.03 (s, 2H), 3.91 (s, 2H), 3.83 (s, 3H).l3 NMR (101 MHz, CDC13) oe 163.2 (dd, J 251.8, 12.7 Hz), 161.6 (d, J= 257.3 Hz), 159.49 (d,J= 50.9 Hz). 149.6, 149.5, 143.7, 134.9, 134.5 (d,J= 3.9 Hz), 132.0, 129.9,129.4, 128.6, 118.4 (d, J= 19.2 Hz), 115.2, 114.2, 114.0, 112.9- 111.0(m), 102.3 (t, J25.3 Hz), 70.1, 55.48 , 38.0.(ESI+) MS: m/z 459.6 (MH+).
  • 15
  • [ 156635-90-4 ]
  • [ 1679-18-1 ]
  • (S)-ethyl 2-(5-bromo-4-chloro-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate [ No CAS ]
  • (S)-ethyl 2-(tert-butoxy)-2-(4-(4-chlorophenyl)-5-(4-((4-methoxybenzyl)oxy)phenyl)-2,6-dimethylpyridin-3-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
A mixture of(S)-ethyl 2-(5-bromo-4-iodo-2,6- dimethylpyridin-3-yl)-2-(tert-butoxy)acetate (0.087 g, 0.185 mmol), (4- chlorophenyl)boronic acid (0.029 g, 0.185 mmol) and 2M Na2CO3 (0.093 ml, 0.185 mmol) in DMF (2 mL) was degassed for 10 mm. Then, Pd(Ph3P)4 (0.02 1 g, 0.0 19 mmol) was added, degassed for 5 mm and placed in pre-heated oil bath at 60 C. After 6 h, <strong>[156635-90-4](4-((4-methoxybenzyl)oxy)phenyl)boronic acid</strong> (0.057 g, 0.222 mmol) was added and heated at 110 C for 2 h. Then, cooled and purified by prep-HPLC to affordpale yellow paste which is a mixture of compounds (0.08 g) and used in the next step without further purification
  • 16
  • [ 156635-90-4 ]
  • [ 5720-05-8 ]
  • (S)-ethyl 2-(5-bromo-4-iodo-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate [ No CAS ]
  • (S)-ethyl 2-(5-bromo-2,6-dimethyl-4-(p-tolyl)pyridin-3-yl)-2-(tert-butoxy)acetate [ No CAS ]
  • (S)-ethyl 2-(tert-butoxy)-2-(5-(4-((4-methoxybenzyl)oxy)phenyl)-2,6-dimethyl-4-(p-tolyl)pyridin-3-yl)acetate [ No CAS ]
  • (S)-ethyl 2-(4,5-bis(4-((4-methoxybenzyl)oxy)phenyl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
A mixture of (S)-ethyl 2-(5 -bromo-4-iodo-2, 6-dimethylpyridin-3 -yl)-2-(tert- butoxy)acetate (0.078 g, 0.166 mmol), p-tolylboronic acid (0.023 g, 0.166 mmol) and 2M Na2CO3 (0.249 ml, 0.498 mmol) in DMF (3 mL) was degassed for 10 mm. Then,PdCl2(dppf)-CH2Cl2Adduct (0.0 14 g, 0.0 17 mmol) was added, degassed for 5 mm and placed in a pre-heated oil bath 60 C. After 6 h, (4-((4- methoxybenzyl)oxy)phenyl)boronic acid (0.064 g, 0.249 mmol) was added and stirred at 90 C for 4 h. Then, cooled and purified by prep-HPLC to afford three products.
  • 17
  • [ 624-31-7 ]
  • [ 156635-90-4 ]
  • C21H20O4S [ No CAS ]
  • 18
  • [ 156635-90-4 ]
  • methyl 5-bromo-4-methoxy-2-oxo-1-[2-(trimethylsilyl)ethoxy]methyl}-1,2-dihydropyridine-3-carboxylate [ No CAS ]
  • methyl 4-methoxy-5-{4-[(4-methoxybenzyl)oxy]phenyl}-2-oxo-1-[2-(trimethylsilyl)ethoxy]methyl}-1,2-dihydropyridine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; at 60℃; for 16h;Inert atmosphere; Schlenk technique; A 25 mL Schlenk tube was loaded with ethyl5-bromo-4-methoxy-2-oxo-1-[2-(trimethylsilyl)ethoxy]methyl}-1,2-dihydropyridine-3-carboxylate (1.764 g, 4.496 mmol, 1.0 equiv), K2CO3 (1.865 g, 13.494 mmol, 3.0 equiv), [Pd(PPh3)4](520 mg, 0.450 mmol, 0.1 equiv) and <strong>[156635-90-4]{4-[(4-methoxybenzyl)oxy]phenyl}boronic acid</strong> (1.743 g, 6.754 mmol, 1.5 equiv). The previously degassed solvent mixture (DME/water/DMF 9/1/0.5; 9 mL)was added. The suspension was frozen in liquid nitrogen and was degassed in three freeze-pumpthaw-cycles. The reactionwas then stirred for 16 h at 60 C. The reaction mixture was diluted with EtOAc (100 mL), washed with a saturated aqueous solution of ammonium chloride (1 100 mL) and with brine (2 100 mL).The organic phase was dried over sodium sulfate, filtered and the solvents were removed in vacuo. The crude product was purified by column chromatography (25% pentane in diethyl ether + 0.1%Et3N). Colorless solid, yield: 92%; Rf = 0.20 (25% pentane in diethylether + 0.1% Et3N); 1H NMR (500 MHz, CDCl3) d 7.37 (m, 2H, 7.34(s, 1H), 7.33 (m, 2H), 6.99 (m, 2H), 6.93 (m, 2H), 5.33 (s, 2H),5.01 (s, 2H), 3.94 (s, 3H), 3.82 (s, 3H), 3.73 (s, 3H), 3.67 (m, 2H),0.95 (m, 2H), 0.00 (s, 9H); 13C NMR (126 MHz, CDCl3) d 166.6,164.0, 161.2, 159.7, 158.7, 136.1, 130.3, 129.4, 128.8, 126.2,116.7, 115.0, 114.2, 111.6, 76.3, 70.0, 67.6, 59.4, 55.4, 53.0, 18.2,1.2; HRMS (ESI+) exact mass calculated for [C28H36NO7Si]+ m/z526.2256 [M+H]+, found m/z 526.2256, [M+H]+; FT-IR ~m (neat,cm1): 2955, 1733, 1612, 1587, 1561, 1518, 1462, 1448, 1401,1389, 1366, 1330, 1308, 1266, 1247, 1208, 1166, 1079, 1056,1036, 1007, 96, 976, 958, 904, 856, 832, 815, 753, 692, 668, 637.
  • 19
  • [ 156635-90-4 ]
  • [ 4068-75-1 ]
  • 2-hydroxy-5-[4-(4-methoxyphenylmethoxy)phenyl]benzoic acid potassium salt [ No CAS ]
  • 20
  • [ 156635-90-4 ]
  • [ 4068-75-1 ]
  • 5-[4'-(4"-methoxybenzyloxy)phenyl]-2-hydroxybenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With palladium diacetate; potassium carbonate; triphenylphosphine; In water; N,N-dimethyl-formamide; at 100℃; for 3h;Microwave irradiation; Inert atmosphere; Sealed tube; Methyl 5-iodosalicylate (50 mg, 0,180 mmol), <strong>[156635-90-4]4-(4'-methoxybenzyloxy)phenylboronic acid</strong>(45 mg, 0,216 mmol), PPh3 (7.1 mg, 0.027 mmol), K2CO3 (87.1 mg, 0.63 mmol), Pd(AcO)2 (2 mg, 0,009 mmol), 1:1 DMF: H2O (2 ml) were used. In this case, prior to chromatographic purification, the residue from evaporating the filtrate was resuspended in methanol. The precipitate was separated from the liquid phase and the latter was discarded. The solid was then purified by flash chromatography (gradient elution with AcOEt: CH3CN:H2O:CH3OH mixtures from 70:10:5:5 to 60:10:10:10). 92 was obtained in the form of a yellowish solid. Yield after purification: 20 % (13 mg). 1H NMR (400 MHz, acetone-d6) delta 8.10 (d, J = 2.4 Hz, 1H), 7.80 (dd, J = 8.7, 2.5 Hz, 1H), 7.57 (d, J = 8.8 Hz, 2H), 7.43 (d, J = 8.6 Hz, 2H), 7.09 (d, J = 8.8 Hz, 2H), 7.04 (d, J = 8.6 Hz, Hz, 1H), 6.96 (d, J = 8.7 Hz, 2H), 5.09 (s, 2H), 3.81 (s, 3H). 13C NMR (101 MHz, acetone-d6) delta 172.6 (CO), 159.4 (C), 135.0 (CH), 133.2 (C), 132.9 (C), 130.2 (CH), 128.6 (CH), 128.4 (CH), 126.8 (C), 118.6 (CH), 116.2 (CH), 114.7 (CH), 113.3 (C), 70.3 (CH2), 55.6 (CH3). HRMS (TOF, ES-): Calculated for C21H17O5 (M-H)-: m/z 349.1076. 349.1084 found (deviation 2.3 ppm). m.p. (C) = 177.8.
  • 21
  • [ 16870-28-3 ]
  • [ 156635-90-4 ]
  • 2-hydroxy-4-[4-(4-methoxyphenylmethoxy)phenyl]benzoic acid potassium salt [ No CAS ]
  • 22
  • [ 1166997-21-2 ]
  • [ 156635-90-4 ]
  • C33H37N3O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; at 90℃; for 3h;Sealed tube; Inert atmosphere; <strong>[156635-90-4](4-((4-methoxybenzyl)oxy)phenyl)boronic acid</strong> (4.4lg, l7.08mmol) was mixed with DME (70mL) in a sealable tube. A 2M solution of sodium carbonate in water (l4.64mL, 29.28mmol) was added followed by a solution of di-tert-butyl [3-(3-(chloromethyl)-l,2-oxazol-5-yl)pyridin-2- yl]imidodicarbonate (Intermediate A, 5.00g, l2.20mmol) in DME (lOmL). Palladium tetrakis triphenylphosphine (l.27g, l. lOmmol) was added and the sealable tube was flushed with argon and sealed. The mixture was stirred for 3h at 90C. The cooled reaction mixture was poured into a stirring mixture of water (300mL) and warm ethyl acetate (500mL). The layers were separated the aqueous phase was further extracted with ethyl acetate (3x 100 mL). The combined organic layers were washed with brine (50 mL), dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Si02, hexane/ethyl acetate) to give the di-Boc protected coupling intermediate (6.00g, l0.2lmmol), which was dissolved in dioxane (60mL). To the resulting solution was added HC1 (4M; lOmL, 40mmol) and the mixture was stirred for 3h at 50C. THF (lOOmL) and toluene (lOOmL) were added and the pH was adjusted to 6-7 by the addition of an aqueous solution of K3P04. The layers were separated the aqueous phase was further extracted with a mixture of ethyl acetate/THF/toluene = 1: 1: 1 (3x 100 mL). The combined organic layers were dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Si02, hexane/ethyl acetate) to yield 4-((5-(2-aminopyridin-3-yl)isoxazol-3-yl)methyl)phenol (2.30g, 8.60mmol, 84%) as a white solid. 400 MHz NMR (DMSO-d6) d 9.30 (s, 1H), 8.08 (dd, J= 4.8, 1.8 Hz, 1H), 7.86 (dd, J= 7.7, 1.9 Hz, 1H), 7.15 - 7.07 (m, 2H), 6.80 - 6.65 (m, 4H), 6.26 (s, 2H), 3.90 (s, 2H). MS: 268.4 [M+H]+.
  • 23
  • [ 156635-90-4 ]
  • [ 769-92-6 ]
  • [ 153059-36-0 ]
  • [ 1258233-74-7 ]
YieldReaction ConditionsOperation in experiment
With [bis(acetoxy)iodo]benzene; sulfuric acid; In methanol; dichloromethane; 1,1,1,3',3',3'-hexafluoro-propanol; Example 79C (2R,3S,4S,5R)-1-(4-tert-butylphenyl)-2,5-bis(4-(4-methoxybenzyloxy)phenyl)-pyrrolidine-3,4-diol To a solution of Example 79B (1.0 g, 4.5 mmol) in CH3OH (12.0 mL) and CH2Cl2 (6.0 mL) was added iodobenzene diacetate (3.48 g, 10.8 mmol) and the solution was stirred at room temperature for 5 h. Solvent was removed in vacuo and to the residue was added 0.1 M H2SO4 (4 mL) and the solution was stirred at room temperature for 18 h. The pH was adjusted to ~6 with solid NaHCO3, and 4-tert-butylaniline (1.43 mL, 9.0 mmol) was added followed by <strong>[156635-90-4]4-(4-methoxybenzyloxy)phenylboronic acid</strong> (2.09 g, 8.1 mmol) and hexafluoroisopropyl alcohol (8 mL). The solution was heated at 50 C. for 2 h, cooled and solvent removed in vacuo leaving the aqueous layer which contained quite a bit of solid material. The mixture was diluted with H2O and 0.33 M K3PO4 was added and the mixture was stirred vigorously. The resulting white solid was collected by filtration and dried in a vacuum oven to give title compound (1.49 g, 2.26 mmol, 50%). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.10 (s, 9H) 3.75 (s, 6H) 4.21 (s, 2H) 4.95 (s, 2H) 5.02 (d, J=6.9 Hz, 2H) 5.75 (s, 2H) 6.20 (d, J=8.9 Hz, 2H) 6.85-6.97 (m, 10H) 7.05 (d, J=8.6 Hz, 4H) 7.37 (d, J=8.7 Hz, 4H).
  • 24
  • [ 1166997-21-2 ]
  • [ 156635-90-4 ]
  • C33H37N3O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 90℃; for 3h;Sealed tube; Inert atmosphere; <strong>[156635-90-4](4-((4-methoxybenzyl)oxy)phenyl)boronic acid</strong> (4.41 g, 17.08 mmol) was mixed with DME (70 mL) in a sealable tube. A 2 M solution of sodium carbonate in water (14.64 mL, 29.28 mmol) was added followed by a solution of di-tert-butyl [3-(3-(chloromethyl)-1,2-oxazol-5-yl)pyridin-2-yl]imidodicarbonate (1, 5.00 g, 12.20 mmol) in DME (10 mL). Palladium(0)tetrakis(triphenylphosphine) (1.27 g, 1.10 mmol) was added and the sealable tube was flushed with argon and sealed. The mixture was stirred for 3 h at 90 C. The cooled reaction mixture was poured into a stirring mixture of water (300 mL) and warm ethyl acetate (500 mL). The layers were separated the aqueous phase was further extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with brine (50 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, hexane/ethyl acetate) to give the di-Boc protected coupling intermediate (6.00 g, 10.21 mmol), which was dissolved in dioxane (60 mL). To the resulting solution was added HCl (4M in water; 10 mL, 40 mmol) and the mixture was stirred for 3 h at 50 C. THF (100 mL) and toluene (100 mL) were added and the pH was adjusted to 6-7 by the addition of an aqueous solution of K3PO4. The layers were separated the aqueous phase was further extracted with a mixture of ethyl acetate/THF/toluene = 1:1:1 (3×100 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, hexane/ethyl acetate) to yield 4-((5-(2-aminopyridin-3-yl)isoxazol-3-yl)methyl)phenol (2.30 g, 8.60 mmol, 84%) as a white solid.
  • 25
  • [ 16870-28-3 ]
  • [ 156635-90-4 ]
  • 4-[4'-(4"-methoxybenzyloxy)phenyl]-2-hydroxybenzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With palladium diacetate; potassium carbonate; triphenylphosphine; In water; N,N-dimethyl-formamide; at 100℃; for 3h;Microwave irradiation; Inert atmosphere; Sealed tube; <strong>[16870-28-3]2-hydroxy-4-iodobenzoic acid</strong> (50 mg, 0.189 mmol), 4-(4'-methoxybenzyloxy)phenylboronic acid (58.6 mg, 0.227 mmol), PPh3 (7.4 mg, 0.028 mmol), K2CO3 (91.4 mg, 0.662 mmol), Pd(AcO)2 (2.12 mg, 0.0095 mmol), 1:1 DMF: H2O (2 ml) were used. Purification was carried out by flash chromatography (gradient elution using AcOEt: CH3CN:H2O: CH3OH from 70:5:2.5:2.5 to 60:10:10:10 mixture) to obtain compound 91 as a solid. Yield after purification: 17 % (11.3 mg). 1H NMR (300 MHz, methanol-d4) delta 7.81 - 7.71 (m, 1H), 7.50 - 7.42 (m, 2H), 7.28 (d, J = 8.5 Hz, 2H), 6.99 - 6.88 (m, 4H), 6.88 - 6.80 (m, 2H), 4.95 (s, 2H, CH2), 3.70 (s, 3H, CH3). 13C NMR (151 MHz, methanol-d4) delta 131.8, 130.3, 129.4, 117.6, 116.3, 114.9, 114.8, 70.8 (CH2), 55.7 (CH3). HRMS (TOF, ES-): Calculated for C21H17O5 (M-H)-: m/z 349.1076. 349.1071 found (deviation 1.4 ppm). m.p. (C) = 199.8.
  • 26
  • [ 156635-90-4 ]
  • [ 1395343-15-3 ]
  • 5-butyl-4-(4-((4-methoxybenzyl)oxy)phenyl)-6-phenylpyrimidin-2-amine [ No CAS ]
Reference: [1]ChemMedChem,2020
  • 27
  • [ 156635-90-4 ]
  • [ 50906-56-4 ]
  • C29H32O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With silver(I) acetate; palladium diacetate; Cs2CO3 In N,N-dimethyl-formamide at 80℃; for 12h; 7.1 Procedure for the synthesis of 3a-3p General procedure: Compounds 1 and 2 were dissolved in 3ml DMF in a dry hard glass tube charged with 0.5mm magnetic bead and of catalyst Pd(OAc)2(10mol %) was added to the solution followed by the addition of AgOAc (2eq.) and base Cs2CO3 (1.5eq.). The reaction mixture was heated at 80°C and meanwhile monitored by TLC. After continuing the reaction for 12h, TLC analysis indicated complete consumption of both the starting materials and formation of the new product. The reaction was then cooled to room temperature and quenched by 5ml of EtOAc and concentrated on vacuum at 80°C for 10min. until all the DMF was evaporated. The product was then washed with brine, collected in EtOAc and dried under vacuum. The resulting crude mixture was purified through silica gel column chromatography using Hexane:EtOAc (9:1) to afford the compounds (3a-3n).
67% With silver(I) acetate; palladium diacetate; Cs2CO3 In N,N-dimethyl-formamide at 80℃; for 12h; 7.1 Procedure for the synthesis of 3a-3p General procedure: Compounds 1 and 2 were dissolved in 3ml DMF in a dry hard glass tube charged with 0.5mm magnetic bead and of catalyst Pd(OAc)2(10mol %) was added to the solution followed by the addition of AgOAc (2eq.) and base Cs2CO3 (1.5eq.). The reaction mixture was heated at 80°C and meanwhile monitored by TLC. After continuing the reaction for 12h, TLC analysis indicated complete consumption of both the starting materials and formation of the new product. The reaction was then cooled to room temperature and quenched by 5ml of EtOAc and concentrated on vacuum at 80°C for 10min. until all the DMF was evaporated. The product was then washed with brine, collected in EtOAc and dried under vacuum. The resulting crude mixture was purified through silica gel column chromatography using Hexane:EtOAc (9:1) to afford the compounds (3a-3n).
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