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[ CAS No. 5735-41-1 ] {[proInfo.proName]}

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Chemical Structure| 5735-41-1
Chemical Structure| 5735-41-1
Structure of 5735-41-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5735-41-1 ]

CAS No. :5735-41-1 MDL No. :MFCD01075677
Formula : C7H7BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :XOQABDOICLHPIS-UHFFFAOYSA-N
M.W : 133.94 Pubchem ID :403788
Synonyms :

Calculated chemistry of [ 5735-41-1 ]

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 : 1.0
Molar Refractivity : 39.04
TPSA : 29.46 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) : -6.46 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.93
Log Po/w (WLOGP) : -0.25
Log Po/w (MLOGP) : 0.22
Log Po/w (SILICOS-IT) : 0.32
Consensus Log Po/w : 0.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.7
Solubility : 2.67 mg/ml ; 0.0199 mol/l
Class : Very soluble
Log S (Ali) : -1.13
Solubility : 9.82 mg/ml ; 0.0733 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.84
Solubility : 1.93 mg/ml ; 0.0144 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.8

Safety of [ 5735-41-1 ]

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 [ 5735-41-1 ]

* 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 [ 5735-41-1 ]

[ 5735-41-1 ] Synthesis Path-Downstream   1~92

  • 1
  • [ 10467-10-4 ]
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  • [ 92987-34-3 ]
  • 2
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  • 3
  • [ 917-64-6 ]
  • [ 5735-41-1 ]
  • [ 96983-90-3 ]
  • 4
  • [ 917-64-6 ]
  • [ 5735-41-1 ]
  • 1-methyl-1,3-dihydro-benzo[<i>c</i>][1,2]oxaborole [ No CAS ]
  • [ 96983-90-3 ]
  • 5
  • [ 64-17-5 ]
  • [ 5735-41-1 ]
  • [ 92987-33-2 ]
  • 6
  • [ 5735-41-1 ]
  • phenylmagnesium bromide [ No CAS ]
  • [ 96217-68-4 ]
  • 7
  • [ 5735-41-1 ]
  • [ 100-51-6 ]
  • [ 96983-89-0 ]
  • 8
  • [ 5735-41-1 ]
  • [ 108-93-0 ]
  • [ 95515-59-6 ]
  • 11
  • [ 5735-41-1 ]
  • [ 118803-40-0 ]
YieldReaction ConditionsOperation in experiment
84% With nitric acid; at -45℃; for 0.5h; Fuming nitric acid (1.49 g, 10 mL) is placed in a 50 mL RBF at -45 C. Benzoboroxole (1.60 g, 11.5 mmol) is added in portions over 40 min with stirring, and the temperature is kept at -45 C for other additional 30 min. The solution is then poured into 20 ml of ice-water. The product precipitates and is stirred for 2 h. The resulting solid is filtered and washed with cold distilled water and then dried under vacuum. Yield: 1.73 g (9.7 mmol, 84%), white solid. 1H NMR (500 MHz, DMSO-d6): delta [ppm]: 9.59 (s, 1H), 8.57 (d, J = 2 Hz, 1H), 8.33 (dd, J = 2. 8 Hz, 1H), 7.69 (dd, J = 1.8 Hz, 1H), 5.12 (s, 2H). 13C NMR (126 MHz, DMSO-d6): delta [ppm] 160.6, 147.1, 125.6, 125.4, 123.0, 70.0. HRMS (ESI, positive, methanol): m/z 180.04639 calculated for C7H7BNO4; [M+H]+ found 180.04678.
68% With nitric acid; at -40℃; for 0.5h; Nitration of benzoboroxole with fuming nitric acid resulted in the formation of 6- nitrobenzoboroxole compound IX.
67% With nitric acid; at -30 - 30℃; for 0.583333h; To a solution of (2-formylphenyl)boronic acid (10 g, 66.69 mmol, 1 eq) in THF (100 ml_) was added NaBH4 in portions (5.05 g, 133.39 mmol, 2 eq) at 0C over 5 min. After addition, the mixture was stirred at 25C for 1 hr. The reaction mixture was quenched by adding aq. HCI (2M) at 0C until pH to 7, and then diluted with EtOAc (30 ml_) and extracted with EtOAc (30 ml_ x 3). The combined organic layers were washed with brine (30 ml_ x 3), dried over Na2S04, filtered and concentrated under reduced pressure to give benzo[c][1 ,2]oxaborol-1 (3H)-ol (7.7 g, 57.49 mmol, 86.2% yield) as a white solid. 1H NMR (CDCI3, 400 MHz): d 7.78 (d, J = 7.2 Hz, 1 H), 7.53-7.49 (m, 1 H), 7.41-7.36 (m, 2 H), 5.75 (s, 1 H) and 5.15 (s, 2 H) ppm. To a solution of fuming HNO3 (70 ml_) was added benzo[c][1 ,2]oxaborol-1(3H)-ol (6.7 g, 50.02 mmol, 1 eq) at -30C over 5 min. After addition, the mixture was stirred at - 30C for 30 min. The reaction mixture was poured with stirring into water and ice (80 ml_) and stirred at 0C for 40 min. Solid was precipitated. The solid was filtered and dried under vacuum to afford 1-hydroxy-6-nitro-3H-2, 1-benzoxaborole (6 g, 33.53 mmol, 67.0% yield, 100% purity) as a pale yellow solid. 1H NMR (DMSO-cfe, 400 MHz): d 9.59 (s, 1 H), 8.57 (s, 1 H), 8.33 (dd, J = 8.4, 2.0 Hz, 1 H), 7.69 (d, J = 8.4 Hz, (0459) 1 H), 5.1 1 (s, 2 H) ppm. MS (ESI): mass calcd. For C7H8BN02 149.06, m/z found 150.1 [M+H]+. Purity by HPLC: 100% (220 nm) and 100% (254 nm). To a solution of 1-hydroxy-6-nitro-3H-2, 1-benzoxaborole (950 mg, 5.31 mmol, 1 eq) in EtOAc (20 ml_) was added Pd/C (200 mg, 10%) under N2. The suspension was degassed under vacuum and purged with H2 several times. The mixture was stirred under H2 (15 psi) at 25C for 2 hrs. The reaction mixture was filtered, and the filtrate was concentrated to give crude product. The crude product was purified by re-crystallization from 20 ml_ of MTBE to give 6-aminobenzo[c][1 ,2]oxaborol-1 (3H)-ol (0.73 g, 4.90 mmol, 92.3% yield, 100% purity) as a pale yellow solid. 1H NMR (DMSO-cfe, 400 MHz): d 8.90 (s, 1 H), 7.03 (d, J = 8.0 Hz, 1 H), 6.87 (s, 1 H), 6.69 (d, J = 8.0 Hz, 1 H), 4.97 (s, 2 H), 4.80 (s, 2 H) ppm. MS (ESI): mass calcd. For C7H8BN02 149.06, m/z found (0460) 150.1 [M+H]+. Purity by HPLC: 100% (220 nm) and 100% (254 nm). To a solution of 6-aminobenzo[c][1 ,2]oxaborol-1 (3H)-ol (1 g, 6.71 mmol, 1 eq) in DMF (15 mL) was added NCS (0.95 g, 7.11 mmol, 1.06 eq) at 0C. The mixture was stirred at 25C for 1.5 hr. The reaction mixture was quenched by adding ice-water (50 mL) at 0C, and then diluted and extracted with EtOAc (10 mL x 3). The combined organic layers were washed with brine (30 mL x 3), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by re (0461) crystallization from MTBE (20 mL) to afford crude product (800 mg, brown solid). (0462) Part of the crude product (270 mg, brown solid) was further purified by prep-TLC (Si02, Ethyl acetate/MeOH=10/1) to give 6-amino-7-chlorobenzo[c][1 ,2]oxaborol- 1 (3H)-ol (44.6 mg, 96.3% purity) was obtained as a yellow solid. 1H NMR (DMSO-cfe, 400 MHz): d 8.89 (s, 1 H), 7.03 (d, J = 8.0 Hz, 1 H), 6.92 (d, J = 8.0 Hz, 1 H), 5.21 (s, (0463) 2 H), 4.82 (s, 2 H) ppm. MS (ESI): mass calcd. For C7H7BCIN02 183.03, m/z found (0464) 184.2 [M+H]+. Purity by HPLC: 96.33% (220 nm).
  • 12
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  • [ 139517-64-9 ]
  • [ 139517-65-0 ]
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  • [ 90-01-7 ]
  • 14
  • [ 109-04-6 ]
  • [ 5735-41-1 ]
  • [ 98061-37-1 ]
  • 15
  • [ 16419-60-6 ]
  • [ 5735-41-1 ]
  • 19
  • [ 5735-41-1 ]
  • [ 125716-22-5 ]
  • 20
  • [ 5735-41-1 ]
  • [ 648905-79-7 ]
  • [2-(2-hydroxymethylphenyl)-6-methoxynaphthalen-1-yl][4-(2-piperidin-1-ylethoxy)phenyl]methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% With sodium carbonate;palladium diacetate; triphenylphosphine; In 1,2-dimethoxyethane; at 20 - 50℃; for 8h; Add Pd [(OAC)] 2 (15 mg, 0.07 mmol) and Ph3P (47 mg, 0.18 mmol) to a stirred solution of trifluoro-methanesulfonic acid [6-METHOXY-1- [4- (2-PIPERIDIN-1-YL-ETHOXY)-] benzoyl] -naphthalen-2-yl ester (600 mg, [1. 1] mmol) in DME at r. t. [ADD NA2C03] solution (2 mL of 2 M) followed by [L-HYDROXY-2,] [1-BENZOXABOROLANE] (200 mg, 1.5 mmol). Stir at r. t. for 2 h and heat gently (-50 C) for 6 h. Dilute with [CH2C12] and wash with water and brine, dry over [MGSO4,] filter and concentrate. Purify the crude product by flash chromatography (0-5% (2M NH3 in [MEOH)/CH2CL2] to yield [2- (2-hydroxymethyl- [ PHENYL) -6-METHOXY-NAPHTHALEN-1-YL]- [4- (2-PIPERIDIN-1-YL-ETHOXY)-PHENYL]-METHANONE (171 MG, 31%).] 'H NMR [((CD13)] : 7.84 (d, J [= 10.] 2 Hz, [1H),] 7.62 (br. s, 2H), 7.2-7. 5 (m, [5H),] 7.0-7. 1 (br. m, 2H), 6.9 (br. s, [1H),] 6. [8] (br. m, 2H), 4.28-4. 48 (br. m, 2H), 4.1 (br. s, 2H), 3.94 (s, 3H), 2.75 (br. [M,] 2H), 2.49 (br. s, 4H), 1.6 (m, 4H), 1.43 (m, 2H)
  • 21
  • [ 866946-41-0 ]
  • [ 5735-41-1 ]
  • (R)-3-(diethylamino)-N-(1-(2'-(hydroxymethyl)biphenyl-4-yl)-1-oxo-4-phenylbutan-2-yl)propane-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 90℃; for 0.75h;Microwave irradiation; Preparation of biaryl sulfonamide 5; A catalytic amount of Pd(PPh3)4 was added to a suspension of the sulfonamide 4 (100mg, 0.2mmol), 2-hydroxylmethylphenyl boronic acid cyclic monoester (53mg, 0.4mmol), K2C03 (55mg, 0.4mmol) in toluene/EtOH/H20 (4ml, 2/1/1) and heated in a microwave (CEM Discover) to 90C for 45mins. The organic layer was extracted with EtOAc (5ml) then washed with brine (5ml), dried over MgS04 and evaporated in vacuo. The product was purified by silica gel column chromatography eluting with a gradient from 0 to 10% MeOH, 1 % NH40H in EtOAc. Yield = 100mg (95%) ¹H NMR CDC13 0.97 (t J = 7.0 Hz, 3H) ; 1.83-2.09 (m, 4H) ; 2.13-2.24 (m, 1H) ;2.46-2.63 (m, 6H) ; 2.84-2.91 (m, 2H) ; 2.93-3.08 (m, 2H) ; 4.58 (s, 2H) ; 5.03-5.13 (m, 1H); 7.19-7.34 (m, 6H) ; 7.37-7.50 (m, 4H) ; 7.56-7.62 (m, 1H); 7.75-7.82 (m, 2H)
  • 23
  • aqueous hydrochloric acid (HCl) [ No CAS ]
  • [ 121-43-7 ]
  • [ 18982-54-2 ]
  • [ 5735-41-1 ]
YieldReaction ConditionsOperation in experiment
0.43 g (21%) With n-butyllithium; In tetrahydrofuran; A. 1,3-Dihydro-1-hydroxy-2,1-benzoxaborole To a solution of 2-bromobenzyl alcohol (2.8 g, 15 mmol) in 30 ml of tetrahydrofuran (THF) under argon at -40C, a 2.0 M solution of butyllithium in hexanes (15.5 ml) was added dropwise over 15 minutes. The solution was stirred for an additional 15 minutes and trimethylborate (3.22 g, 31.0 mmol) was added. After 15 minutes at -40C, the solution was warmed to room temperature and stirred for a further 2 hours. The reaction was quenched by the addition of 10% aqueous hydrochloric acid (HCl) (100 ml), and after 10 minutes, the solution was extracted with ethyl acetate (3 x 75 ml). The combined ether extracts were then extracted with 2N aqueous sodium hydroxide (NaOH) (3 x 50 ml). The aqueous extracts were then acidified with dilute hydrochloric acid to pH 2 and extracted with 3 x 50 ml of ethyl acetate. The combined organic extracts were washed once with water (100 ml), dried and evaporated to afford 0.43 g (21%) of compound A as a white solid (m.p. 138 - 140C).
  • 24
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  • [ 156386-82-2 ]
  • [ 1005327-30-9 ]
  • 38
  • [ 1256954-44-5 ]
  • [ 5735-41-1 ]
  • [ 110409-93-3 ]
  • 39
  • [ 40138-16-7 ]
  • [ 5735-41-1 ]
YieldReaction ConditionsOperation in experiment
87% With sodium tetrahydroborate; In tetrahydrofuran; water; at 25℃; for 3h; The reaction of commercially available o-boronobenzaldehyde compound I with sodium borohydride in THF and water provided benzoboroxole compound VIII in 87% yield.
86.2% With sodium tetrahydroborate; In tetrahydrofuran; at 0 - 25℃; for 1.08333h; To a solution of (2-formylphenyl)boronic acid (10 g, 66.69 mmol, 1 eq) in THF (100 ml_) was added NaBH4 in portions (5.05 g, 133.39 mmol, 2 eq) at 0C over 5 min. After addition, the mixture was stirred at 25C for 1 hr. The reaction mixture was quenched by adding aq. HCI (2M) at 0C until pH to 7, and then diluted with EtOAc (30 ml_) and extracted with EtOAc (30 ml_ x 3). The combined organic layers were washed with brine (30 ml_ x 3), dried over Na2S04, filtered and concentrated under reduced pressure to give benzo[c][1 ,2]oxaborol-1 (3H)-ol (7.7 g, 57.49 mmol, 86.2% yield) as a white solid. 1H NMR (CDCI3, 400 MHz): d 7.78 (d, J = 7.2 Hz, 1 H), 7.53-7.49 (m, 1 H), 7.41-7.36 (m, 2 H), 5.75 (s, 1 H) and 5.15 (s, 2 H) ppm. To a solution of fuming HNO3 (70 ml_) was added benzo[c][1 ,2]oxaborol-1(3H)-ol (6.7 g, 50.02 mmol, 1 eq) at -30C over 5 min. After addition, the mixture was stirred at - 30C for 30 min. The reaction mixture was poured with stirring into water and ice (80 ml_) and stirred at 0C for 40 min. Solid was precipitated. The solid was filtered and dried under vacuum to afford 1-hydroxy-6-nitro-3H-2, 1-benzoxaborole (6 g, 33.53 mmol, 67.0% yield, 100% purity) as a pale yellow solid. 1H NMR (DMSO-cfe, 400 MHz): d 9.59 (s, 1 H), 8.57 (s, 1 H), 8.33 (dd, J = 8.4, 2.0 Hz, 1 H), 7.69 (d, J = 8.4 Hz, (0459) 1 H), 5.1 1 (s, 2 H) ppm. MS (ESI): mass calcd. For C7H8BN02 149.06, m/z found 150.1 [M+H]+. Purity by HPLC: 100% (220 nm) and 100% (254 nm). To a solution of 1-hydroxy-6-nitro-3H-2, 1-benzoxaborole (950 mg, 5.31 mmol, 1 eq) in EtOAc (20 ml_) was added Pd/C (200 mg, 10%) under N2. The suspension was degassed under vacuum and purged with H2 several times. The mixture was stirred under H2 (15 psi) at 25C for 2 hrs. The reaction mixture was filtered, and the filtrate was concentrated to give crude product. The crude product was purified by re-crystallization from 20 ml_ of MTBE to give 6-aminobenzo[c][1 ,2]oxaborol-1 (3H)-ol (0.73 g, 4.90 mmol, 92.3% yield, 100% purity) as a pale yellow solid. 1H NMR (DMSO-cfe, 400 MHz): d 8.90 (s, 1 H), 7.03 (d, J = 8.0 Hz, 1 H), 6.87 (s, 1 H), 6.69 (d, J = 8.0 Hz, 1 H), 4.97 (s, 2 H), 4.80 (s, 2 H) ppm. MS (ESI): mass calcd. For C7H8BN02 149.06, m/z found (0460) 150.1 [M+H]+. Purity by HPLC: 100% (220 nm) and 100% (254 nm). To a solution of 6-aminobenzo[c][1 ,2]oxaborol-1 (3H)-ol (1 g, 6.71 mmol, 1 eq) in DMF (15 mL) was added NCS (0.95 g, 7.11 mmol, 1.06 eq) at 0C. The mixture was stirred at 25C for 1.5 hr. The reaction mixture was quenched by adding ice-water (50 mL) at 0C, and then diluted and extracted with EtOAc (10 mL x 3). The combined organic layers were washed with brine (30 mL x 3), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by re (0461) crystallization from MTBE (20 mL) to afford crude product (800 mg, brown solid). (0462) Part of the crude product (270 mg, brown solid) was further purified by prep-TLC (Si02, Ethyl acetate/MeOH=10/1) to give 6-amino-7-chlorobenzo[c][1 ,2]oxaborol- 1 (3H)-ol (44.6 mg, 96.3% purity) was obtained as a yellow solid. 1H NMR (DMSO-cfe, 400 MHz): d 8.89 (s, 1 H), 7.03 (d, J = 8.0 Hz, 1 H), 6.92 (d, J = 8.0 Hz, 1 H), 5.21 (s, (0463) 2 H), 4.82 (s, 2 H) ppm. MS (ESI): mass calcd. For C7H7BCIN02 183.03, m/z found (0464) 184.2 [M+H]+. Purity by HPLC: 96.33% (220 nm).
  • 40
  • [ 5735-41-1 ]
  • [ 202865-85-8 ]
  • [ 1307795-18-1 ]
YieldReaction ConditionsOperation in experiment
To a 2:1 (v/v) toluene: ethanol solution (0.25 M) of 2,l-benzoxaborol-l(3H)-ol (1 eq.) and <strong>[202865-85-8]2-bromo-5-iodotoluene</strong> (1.2 eq.) was added was added trans- bis(triphenylphosphine) palladium(II) bromide (0.02 eq.). The vessel was repeatedly evacuated and back-filled with nitrogen. Finally, Na2C03 (2 M aq. solution, 3 eq.) was added and the resulting mixture was heated at 50 C for 12 h. The now black suspension was cooled to RT, diluted with ether and quenched with 10% aq. HC1. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were then washed further with 1 N aq. NaOH, water and brine, dried over Na2S04, filtered and the filtrate concentrated in vacuo. Purification of the crude product by way of flash chromatography (Si02, Hex - 1 :1 (v/v) Hex: EtOAc) afforded the title compound as a golden, yellow oil.
  • 41
  • [ 5735-41-1 ]
  • [ 1307795-20-5 ]
  • 42
  • [ 5735-41-1 ]
  • [ 1307795-22-7 ]
  • 43
  • [ 5735-41-1 ]
  • rac-tert-butyl (3S,4R)-4-[2-(1,3-dioxolan-2-yl)-4,5-difluorophenyl]-4-hydroxy-3-(3-methyl-2'-[(triisopropylsilyl)oxy]methyl}-4-biphenylyl)-1-piperidinecarboxylate [ No CAS ]
  • 44
  • [ 5735-41-1 ]
  • rac-tert-butyl (1R,3'S)-5,6-difluoro-3-hydroxy-3'-(3-methyl-2'-[(triisopropylsilyl)oxy]methyl}-4-biphenylyl)-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 45
  • [ 5735-41-1 ]
  • rac-tert-butyl (3S,4R)-4-[4,5-difluoro-2-(hydroxymethyl)phenyl]-4-hydroxy-3-(3-methyl-2'-[(triisopropylsilyl)oxy]methyl}-4-biphenylyl)-1-piperidinecarboxylate [ No CAS ]
  • 46
  • [ 5735-41-1 ]
  • rac-tert-butyl (1R,3'S)-5,6-difluoro-3'-(3-methyl-2'-[(triisopropylsilyl)oxy]methyl}-4-biphenylyl)-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 47
  • [ 5735-41-1 ]
  • rac-tert-butyl (1R,3'S)-5,6-difluoro-3'-[2'-(hydroxymethyl)-3-methyl-4-biphenylyl]-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 48
  • [ 5735-41-1 ]
  • rac-(1R,3'S)3'-[2'-(tert-butoxymethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-3H-spiro[2-benzofuran-1,4'-piperidine] [ No CAS ]
  • 49
  • [ 5735-41-1 ]
  • rac-{4'-[(1R,3'S)-5,6-difluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3'-yl]-3'-methyl-2-biphenylyl}methanol [ No CAS ]
  • 50
  • [ 5735-41-1 ]
  • rac-tert-butyl (1R,3'S)-(5,6-difluoro-3'-(3-methyl-2'-[methylsulfonyl]oxy}methyl)-4-biphenylyl)-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 51
  • [ 5735-41-1 ]
  • rac-tert-butyl (1R,3'S)-3'-[2'-(cyanomethyl)-3-methyl-4-biphenylyl]-5,6-difluoro-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 52
  • [ 5735-41-1 ]
  • rac-{4'-[(1R,3'S)-5,6-difluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3'-yl]-3'-methyl-2-biphenylyl}acetonitrile [ No CAS ]
  • 53
  • [ 5735-41-1 ]
  • rac-tert-butyl (1R,3'S)-3,-{2'-[2-(acetylamino)ethyl]-3-methyl-4-biphenylyl}-5,6-difluoro-1'H,3H-spiro[2-benzofuran-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 54
  • [ 5735-41-1 ]
  • C32H36F2N2O3 [ No CAS ]
  • 55
  • [ 5735-41-1 ]
  • rac-N-(2-{4'-[(1R,3'S)-5,6-difluoro-3H-spiro[2-benzofuran-1,4'-piperidin]-3'-yl]-3'-methyl-2-biphenylyl}ethyl)acetamide [ No CAS ]
  • 56
  • [ 5735-41-1 ]
  • rac-tert-butyl (3S,4R)-4-hydroxy-4-(2-methoxy-5-[(triisopropylsilyl)oxy]methyl}-4-pyridinyl)-3-(3-methyl-2'-[(triisopropylsilyl)oxy]methyl}-4-biphenylyl)-1-piperidinecarboxylate [ No CAS ]
  • 57
  • [ 5735-41-1 ]
  • rac-tert-butyl (3S,4R)-4-hydroxy-4-[5-(hydroxymethyl)-2-methoxy-4-pyridinyl]-3-[2'-(hydroxymethyl)-3-methyl-4-biphenylyl]-1-piperidinecarboxylate [ No CAS ]
  • 58
  • [ 5735-41-1 ]
  • rac-tert-butyl (1R,3'S)-6-methoxy-3'-(3-methyl-2'-[(methylsulfonyl)oxy]methyl}-4-biphenylyl)-1'H,3H-spiro[furo[3,4-c]pyridine-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 59
  • [ 5735-41-1 ]
  • rac-tert-butyl (1R,3'S)-3'-[2'-(iodomethyl)-3-methyl-4-biphenylyl]-6-methoxy-1H,3H-spiro[furo[3,4-c]pyridine-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 60
  • [ 5735-41-1 ]
  • rac-tert-butyl (1R,3'S)-3'-[2'-(3-tert-butoxy-3-oxopropyl)-3-methyl-4-biphenylyl]-6-methoxy-1'H,3H-spiro[furo [3,4-c]pyridine-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 61
  • [ 5735-41-1 ]
  • rac-tert-butyl (1R,3'S)-3'-[2'-(3-hydroxypropyl)-3-methyl-4-biphenylyl]-6-methoxy-1'H,3H-spiro[furo[3,4-c]pyridine-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 62
  • [ 5735-41-1 ]
  • rac-tert-butyl (1R,3'S)-3'-[2'-(3-methoxypropyl)-3-methyl-4-biphenylyl]-5-methyl-6-oxo-5,6-dihydro-1H,3H-spiro[furo[3,4-c]pyridine-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 63
  • [ 5735-41-1 ]
  • rac-(1R,3'S)-3'-[2'-(3-methoxypropyl)-3-methyl-4-biphenylyl]-5-methyl-3,5-dihydro-6H-spiro[furo[3,4-c]pyridine-1,4'-piperidin]-6-one [ No CAS ]
  • 64
  • [ 5735-41-1 ]
  • rac-tert-butyl (1R,3'S)-3'-[2'-(5-tert-butoxy-3,5-dioxopentyl)-3-methyl-4-biphenylyl]-6-methoxy-1H,3H-spiro[furo[3,4-c]pyridine-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 65
  • [ 5735-41-1 ]
  • rac-tert-butyl (1R,3'S)-3'-[2'-(5-tert-butoxy-3,5-dioxopentyl)-3-methyl-4-biphenylyl]-5-methyl-6-oxo-5,6-dihydro-1H,3H-spiro[furo[3,4-c]pyridine-1,4'-piperidine]-1'-carboxylate [ No CAS ]
  • 66
  • [ 5735-41-1 ]
  • rac-(1R,3'S)-5-methyl-3'-[3-methyl-2'-(3-oxobutyl)-4-biphenylyl]-3,5-dihydro-6H-spiro[furo[3,4-c]pyridine-1,4'-piperidin]-6-one [ No CAS ]
  • 70
  • [ 118-44-5 ]
  • [ 40138-16-7 ]
  • [ 1350570-67-0 ]
  • [ 5735-41-1 ]
YieldReaction ConditionsOperation in experiment
56% To a 100 ml flask equipped with a stir bar, MeCN (24 ml), molecular sieves (3 A, 2.4 g), 2-formylphenylboronic acid (1) (0.788 g, 5.259 mmol), and N-ethyl-1-naphthylamine (0.300 g, 1.752 mmol) were added. The flask was placed in an ice bath and the mixture was stirred for 3 h at 0 C after which the reducing agent, NaBH(OAc)3, (1.112 g, 5.259 mmol) was added. Stirring was continued for another 10 min, and the molecular sieves were removed by filtration. The filtrate was concentrated under reduced pressure and the residue was dissolved in 3 M HCl (4 ml) and H2O (10 ml) and stirred for 10 min. Extraction was carried out with Et2O (4 × 15 ml). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford 4. The pH of the aqueous phase was adjusted to 7 with 25% aq NH3 and the resulting pink precipitate was filtered to afford 3b (0.207 g, 38% yield). An analogous reaction carried out in the presence of an equimolar amount of AcOH resulted in 0.303 g (56% yield) of the desired product. Pink powder (mp = 119-130 C). Crystallization from CDCl3 afforded colorless crystals suitable for X-ray measurements. Elemental analysis calculated for the acid: C19H20BNO2 (305.18): C, 74.78; H, 6.61; N, 4.59; found: C, 74.66; H, 6.66; N, 4.60. 1H NMR (CDCl3 with one drop of D2O, 400 MHz): 8.13 (d, J = 8.3 Hz, 1H, Ar); 7.86 (d, J = 6.8 Hz, 1H, Ar); 7.81 (d, J = 8.0 Hz, 1H, Ar); 7.65-7.63 (m, 1H, Ar); 7.53-7.50 (m, 1H, Ar); 7.48-7.40 (m, 3H, Ar); 7.33-7.27 (m, 3H, Ar); 4.44 (s, 2H, CH2); 3.28 (q, J = 7.2 Hz, 2H, CH2); 0.97 (t, J = 7.2 Hz, 3H, CH3). 13C NMR (CDCl3 with one drop of D2O, 100 MHz): 144.1, 141.2, 136.2, 134.8, 131.5, 130.2, 129.5, 128.7, 127.4, 126.1, 125.9, 125. 8, 125.0, 122.8, 119.7, 57.5, 49.3, 9.3. 11B NMR (CDCl3 with one drop of D2O, 64 MHz): 29.3, 20.0 (minor intensity).
  • 71
  • [ 40138-16-7 ]
  • [ 103-69-5 ]
  • [ 1312999-27-1 ]
  • [ 5735-41-1 ]
YieldReaction ConditionsOperation in experiment
66%Spectr.; 23% To a 50 ml flask equipped with a stir bar, MeCN (10 ml), molecular sieves (3 A, 1 g), 2-formylphenylboronic acid (1) (0.200 g, 1.334 mmol), N-ethylaniline (2) (0.0808 g, 0.667 mmol), and AcOH (0.0801 g, 1.334 mmol) were added. The flask was placed in an ice bath and the mixture was stirred for 3 h at 0 C after which NaBH(OAc)3 (0.283 g, 1.334 mmol) was added. Stirring was continued for another 10 min, and the molecular sieves were removed by filtration. The filtrate was concentrated under reduced pressure and the residue was dissolved in 3 M HCl (4 ml) and H2O (10 ml) and stirred for 5 min. Extraction was carried out with Et2O (4 × 15 ml). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to afford product 4. The pH of the aqueous phase was adjusted to 7 with 25% aq NH3 and extraction was carried out with Et2O (4 × 15 ml). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to afford product 3 (highest yield was 66%). The product was isolated in the form of the anhydride contaminated with 3, which was confirmed on the basis of elemental analysis as well as the 1H NMR spectrum. The spectrum of the pure acid was obtained after the addition of one drop of D2O. Yellow crystals (mp = 84-89 C for the anhydride contaminated with 3). Elemental analysis calculated for the anhydride: C45H48B3N3O3 (711.4) C, 75.98; H, 6.80; N, 5.91; and for 3: C15H18BNO2 (255.14): C, 70.62; H, 7.11; N, 5.49; found: C, 74.03; H, 6.84; N, 5.71. 1H NMR [(CD3)2CO with one drop of D2O, 400 MHz]: 7.72 (m, 1H, Ar); 7.26-7.13 (m, 5H, Ar); 6.91 (m, 2H, Ar); 6.75 (m, 1H, Ar); 4.52 (s, 2H, CH2); 3.30 (q, J = 7.2 Hz, 2H, CH2); 1.03 (t, J = 7.2 Hz 3H, CH3). 13C NMR [(CD3)2CO with one drop of D2O, 100 MHz]: 149.3, 143.6, 135.9, 130.1, 129.6, 128.6, 126.8, 120.0, 117.5, 56,7, 46.6, 11.5. 11B NMR [(CD3)2CO with one drop of D2O, 64 MHz]: 29.6, 20.0 (100:14).
  • 72
  • [ 40138-16-7 ]
  • [ 100-61-8 ]
  • [ 172940-58-8 ]
  • [ 5735-41-1 ]
YieldReaction ConditionsOperation in experiment
43% To a 250 ml flask equipped with a stir bar, MeCN (185 ml), molecular sieves (3 A, 18 g), 2-formylphenylboronic acid (1) (5.600 g; 37.371 mmol), N-methylaniline (2.000 g, 18.665 mmol), and Ac2O (3.815 g, 37.371 mmol) were added. The flask was placed in an ice bath and the mixture was stirred for 3 h at 0 C after which NaBH(OAc)3 (7.900 g, 37.371 mmol) was added. Stirring was continued for another 10 min, and the molecular sieves were removed by filtration. The filtrate was concentrated under reduced pressure and the residue was dissolved in 3 M HCl (8 ml) and H2O (150 ml) and stirred for 5 min. Extraction was carried out with Et2O (4 × 25 ml). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to afford product 4. The pH of the aqueous phase was adjusted to 7 with 25% aq NH3 and the resulting white precipitate was filtered to afford 3a (1.953 g, 43% yield). White powder (mp = 89-95 C). Elemental analysis calculated for the acid: C14H16BNO2 (241.10): C, 69.75; H, 6.69; N, 5.81; found: C, 69.52; H, 6.62; N, 5.85. The 1H NMR spectrum in CDCl3 revealed signals corresponding to the acid as well as to boroxin. Addition of one drop of D2O resulted in the spectrum of pure boronic acid. 1H NMR (CDCl3, 400 MHz): 7.93 (1H, Ar); 7.82 (d, J = 6.9 Hz, 1H, Ar); 7.36-7.33 (m, 6H, Ar); 7.26-7.20 (m, 7H, Ar); 6.93-6.83 (m, 2H, Ar); 4.68 (s, 6H, 3 × CH2); 4.22 (s, 2H, CH2); 2.96 (s, 9H, 3 × CH3); 2.66 (s, 3H, CH3).Comment1H NMR (CDCl3 with one drop of D2O, 400 MHz): 7.95-7.93 (m, 1H, Ar); 7.36-7.31 (m, 4H, Ar); 7.22-7.18 (m, 3H, Ar); 7.08 (t, J = 7.2 Hz, 1H, Ar); 4.22(s, 2H, CH2); 2.66 (s, 3H, CH3). 13C NMR (CDCl3 with one drop of D2O, 100 MHz): 150.5, 141.4, 136.3, 131.0, 130.4, 129.3, 127.6, 123.7, 120.3, 62.4, 40.4. 11B NMR (CDCl3 with one drop of D2O, 64 MHz) 29.0 (br s), 20.0 (minor intensity).
  • 73
  • [ 5735-41-1 ]
  • [ 1361132-00-4 ]
  • 74
  • [ 5735-41-1 ]
  • [ 1361132-01-5 ]
  • 75
  • [ 5735-41-1 ]
  • [ 1361132-12-8 ]
  • 76
  • [ 5735-41-1 ]
  • (4bRS,10bRS)-1',3'-dimethyl-6,10b,11,12-tetrahydro-1'H,4bH-spiro[chrysene-5,5'-pyrimidine]-2',4',6'(3'H)-trione [ No CAS ]
  • 77
  • [ 5735-41-1 ]
  • [ 143139-14-4 ]
  • [ 1361131-99-8 ]
  • 78
  • [ 110-91-8 ]
  • [ 40138-16-7 ]
  • [ 5735-41-1 ]
  • [2-(morpholin-4-ylmethyl)phenyl]boronic acid [ No CAS ]
  • 79
  • [ 892848-97-4 ]
  • [ 5735-41-1 ]
  • [2-(morpholin-4-ylmethyl)phenyl]boronic acid [ No CAS ]
  • 80
  • [ 1357485-60-9 ]
  • [ 5735-41-1 ]
  • [ 1357485-61-0 ]
  • 81
  • [ 5735-41-1 ]
  • [ 1357485-49-4 ]
  • 82
  • [ 5735-41-1 ]
  • [ 1357485-51-8 ]
  • [ 1357485-50-7 ]
  • 83
  • [ 5735-41-1 ]
  • [ 1357485-62-1 ]
  • 84
  • [ 5735-41-1 ]
  • [ 1357485-63-2 ]
  • 85
  • [ 5735-41-1 ]
  • [ 1357485-43-8 ]
  • 86
  • C29H26NO6P [ No CAS ]
  • [ 5735-41-1 ]
  • [ 1384384-78-4 ]
  • 87
  • C31H30NO8P [ No CAS ]
  • [ 5735-41-1 ]
  • [ 1384384-80-8 ]
  • 88
  • [ 130-22-3 ]
  • [ 5735-41-1 ]
  • C21H11BO8S(2-) [ No CAS ]
  • 89
  • [ 377780-72-8 ]
  • [ 5532-69-4 ]
  • [ 1447933-57-4 ]
  • [ 5735-41-1 ]
  • 90
  • [ 10546-67-5 ]
  • [ 5735-41-1 ]
  • 4-t-butyl-2,6-bis[(2'-hydroxymethyl)phenyl]aniline [ No CAS ]
  • 91
  • [ 5735-41-1 ]
  • [ 1005-37-4 ]
  • {2-[2-amino-6-(methylamino)pyrimidin-4-yl]phenyl}methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; acetonitrile; at 120℃; for 0.166667h;Microwave irradiation; Example 508 {2-[2-amino-6-(methylamino)pyrimidin-4-yl]phenyl}methanol <strong>[1005-37-4]6-chloro-4-N-methylpyrimidine-2,4-diamine</strong> (20 mg, 0,13 mmol), 1 ,3-dihydro-2, 1- benzoxaborol-1-ol (25 mg, 0, 19 mmol), K2C03 (78 mg, 0,57 mmol), Tetrakis(triphenylphosphine)palladium(0) (7,3 mg, 0,0060 mmol), MeCN (1 ,5 mL) and water (0,5 mL) were heated in the micro for 10 min at 120C. The organic phase was filtered and purified by basic prep-HPLC to afford {2-[2-amino-6- (methylamino)pyrimidin-4-yl]phenyl}methanol. LCMS [M+H]+ 231
  • 92
  • [ 363-52-0 ]
  • [ 5735-41-1 ]
  • C13H9BFO3(1-) [ No CAS ]
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