868755-79-7|2-(4-(Furan-2-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane| Ambeed

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Quality Control of [ 868755-79-7 ] Purity: 95% SDS Specification

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Product Details of [ 868755-79-7 ]

CAS No. :	868755-79-7
Formula :	C₁₆H₁₉BO₃
M.W :	270.13
SMILES Code :	CC1(C)C(C)(C)OB(C2=CC=C(C3=CC=CO3)C=C2)O1
MDL No. :	MFCD08435855
InChI Key :	PUCSCLCOEROOCP-UHFFFAOYSA-N
Pubchem ID :	18525723

Safety of [ 868755-79-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 868755-79-7 ]

* 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 [ 868755-79-7 ]

[ 868755-79-7 ] Synthesis Path-Downstream 1~11

1
[ 59147-02-3 ]
[ 868755-79-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1397 - 1401.

2
[ 28123-72-0 ]
[ 868755-79-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1397 - 1401.

3
[ 17763-80-3 ]
[ 868755-79-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1397 - 1401.

4
4-(furan-2-yl)iodobenzene [ No CAS ]
[ 25015-63-8 ]
[ 868755-79-7 ]

Yield	Reaction Conditions	Operation in experiment
71%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; triethylamine; In 1,4-dioxane; at 80.0℃;	General procedure: To a 100mL round bottom flask charged with 220mg (0.9mmol) of 4-propyliodobenzene (7c) in 4.5mL dioxane (0.2M) was added palladium(II) acetate (10mg, 0.05mmol, 0.05eq), S-PHOS6 (75mg, 0.18mmol, 0.2eq), and triethylamine (0.5mL, 3.6mmol, 4eq). Under stirring, pinacolborane was added (0.4mL, 2.7mmol, 3eq), whereupon the solution turned black, with notable gas evolution. The reaction was heated to 80oC and stirred overnight. After cooling to room temperature, the reaction was quenched with CH2Cl2 (further gas evolution), plugged through a pad of celite (eluting with CH2Cl2), and purified by flash chromatography (2.5% Ether in Hexanes) to afford the title compound as a clear, colorless oil (150mg, 0.6mmol, 66% yield). GC-MS: RT=8.38min, M/Z: 246.15, 245.15 (35%), 247.05 (16%), 244.15 (3%). 1H NMR (300MHz, CDCl3): 7.73 (d, J=8Hz, 2H), 7.19 (d, J=8Hz, 2H), 2.60 (t, J=7Hz, 2H), 1.64 (sextet, J=7Hz, 2H), 1.34 (s, 12H), 0.93 (t, J=7Hz, 3H). 11B NMR (95MHz, CDCl3): 11.47 (s, br). 13C NMR (75MHz, CDCl3): 146.24, 134.88, 128.04, 83.69, 38.35, 24.51, 13.90.

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1397 - 1401.

5
[ 868755-79-7 ]
C₁₃H₁₄ClN₅ [ No CAS ]
C₂₃H₂₁N₅O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; at 100.0℃; for 0.666667h;Inert atmosphere; Microwave irradiation;	Preparation of compound (55) To a solution of intermediate (18) (170 mg, 0.62 mmol) in DME (3mL) was added 2-(4-(2- furanyl)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (174 mg, 0.64 mmol ) and potassium carbonate solution 2M (0.7 mL, 1.3 mmol) the reaction mixture was degazed with nitrogen for 15 minutes then tetrakis(triphenylphosphine)palladium(0) (7 mg, 0.006 mmol) was added and the mixture was heated at 100C using a single mode microwave (Biotage Initiator EXP 60) with a power output ranging from 0 to 400 W for 40 minutes. Water was added and the product was extracted with ethyl acetate, the organic layer was washed twice with water, then brine, dried over MgS04, filtered and the solvent was evaporated to afford 220 mg of a crude product. The crude product was purified by preparative LC on (Stability Silica 5μιη 150x30.0mm), mobile phase (gradient from 0.2% NH4OH, 2% MeOH, 98% CH2C12 to 0.8% NH4OH, 8% MeOH, 92%) CH2C12). The pure fractions were collected, the solvent was evaporated and the resulting product was crystallized from diethyl ether, filtered and dried to give (0.026 g, 11%) of compound (55). 1H NMR (500 MHz, DMSO-d6) δ 8.25 (d, J= 2.5 Hz, 1H), 8.21 (d, J= 2.5 Hz, 1H), 8.15 (d, J= 6.3 Hz, 2H), 8.02 (d, J= 8.5 Hz, 2H), 7.83 (d, J= 8.5 Hz, 2H), 7.80 (d, J= 1.1 Hz, 1H), 7.05 (d, J= 3.2 Hz, 1H), 6.82 (d, J= 6.3 Hz, 2H), 6.64 (dd, J= 1.1, 3.2 Hz, 1H), 3.35 - 3.41 (m, 4H), 3.22 - 3.28 (m, 4H).

References: [1]Patent: WO2015/14836,2015,A1 .Location in patent: Page/Page column 41; 42.

6
[ 868755-79-7 ]
C₁₄H₁₅ClN₄ [ No CAS ]
C₂₄H₂₂N₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; at 100.0℃; for 0.5h;Inert atmosphere; Microwave irradiation;	Preparation of compound (56) The reaction was performed under nitrogen atmosphere. A solution of intermediate (1) (0.80 g, 2.912mmol) and 4-(fur-2-yl) benzeneboronic acid pinacol ester (1.81 g, 6.7 mmol) in potassium carbonate solution 2M (2.91mL , 5.823 mmol) and DME (12 mL) was purged with nitrogen for 5 minutes then tetrakis (triphenylphosphine) palladium (0.336 g, 0.291 mmol) was added, the mixture was heated at 100C using a singlemode microwave (Biotage initiator 60) with a power output ranging from 0 to 400 W for 30 minutes. The mixture was poured out into water and CH2CI2, the organic layer was separated, washed with water, dried over MgS04 and evaporated till dryness to give 2.50 g of a crude product. The crude product was purified by preparative LC on (Irregular SiOH 20-45 μιη 45 Og MATREX), mobile phase (40% heptane, 10% MeOH (+ 10% NH4OH), 50% AcOEt). The good fractions are collected and the solvent was evaporated to give 0.78 g of the awaited compound, this was triturated from diethyl- ether, filtered and dried under vacuum at 60C, yielding 0.72 g (64%>) of compound (56). 1H NMR (500 MHz, DMSO-d6) δ 8.33 (d, J= 4.5 Hz, 1H), 8.14 (d, J= 6.3 Hz, 2H), 8.08 (d, J= 8.51 Hz, 2H), 7.73 - 7.85 (m, 3H), 7.54 (d, J= 7.6 Hz, 1H), 7.33 (dd, J= 4.5, 7.6 Hz, 1H), 7.01 (d, J= 3.2 Hz, 1H), 6.82 (d, J= 6.3 Hz, 2H), 6.62 (dd, J= 1.6, 3.2 Hz, 1H), 3.26 - 3.40 (m, 4H), 2.87 - 3.02 (m, 4H).

References: [1]Patent: WO2015/14836,2015,A1 .Location in patent: Page/Page column 37.

7
[ 106-40-1 ]
[ 868755-79-7 ]