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[ CAS No. 73183-34-3 ]

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Chemical Structure| 73183-34-3
Chemical Structure| 73183-34-3
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CAS No. :73183-34-3 MDL No. :MFCD00799570
Formula : C12H24B2O4 Boiling Point : 222.6°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :253.94 g/mol Pubchem ID :2733548
Synonyms :

Safety of [ 73183-34-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 73183-34-3 ]

  • Upstream synthesis route of [ 73183-34-3 ]
  • Downstream synthetic route of [ 73183-34-3 ]

[ 73183-34-3 ] Synthesis Path-Upstream   1~37

  • 1
  • [ 80866-82-6 ]
  • [ 73183-34-3 ]
  • [ 1009303-77-8 ]
Reference: [1] Patent: WO2007/80382, 2007, A1, . Location in patent: Page/Page column 131
  • 2
  • [ 84539-30-0 ]
  • [ 73183-34-3 ]
  • [ 1005009-98-2 ]
Reference: [1] Patent: WO2007/86800, 2007, A1, . Location in patent: Page/Page column 92-93
[2] Patent: WO2009/16460, 2009, A2, . Location in patent: Page/Page column 62-63
  • 3
  • [ 151049-87-5 ]
  • [ 73183-34-3 ]
  • [ 1020174-04-2 ]
YieldReaction ConditionsOperation in experiment
44.19% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 95℃; for 5 h; Inert atmosphere Intermediate 702: 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
Compound 701 (0.2 g, 1.24 mmol) was dissolved in 5 ml of 1,4-dioxane, added with 0.378 g (1.49 mmol) of bis(pinacolato)diboron, 0.365 g (3.72 mmol) of potassium acetate, and 0.11 g (0.124 mmol) of [1,1-bis(di-phenylphosphino)ferrocene]palladium chloride dichloromethane complex under the protection of nitrogen, heated to 95 °C and reacted for 5 h, and then cooled to room temperature. 15 mL of water was added, stirred for 1 h, and filtered to afford 0.114 g of solid. Yield: 44.19percent.
Reference: [1] Patent: EP3072893, 2016, A1, . Location in patent: Paragraph 0394; 0395
[2] Patent: EP2818473, 2014, A1, . Location in patent: Paragraph 0578
  • 4
  • [ 123843-67-4 ]
  • [ 73183-34-3 ]
  • [ 1003298-73-4 ]
Reference: [1] Patent: WO2010/59658, 2010, A1, . Location in patent: Page/Page column 205
[2] Patent: WO2007/134828, 2007, A1, . Location in patent: Page/Page column 68-69
  • 5
  • [ 1340571-52-9 ]
  • [ 73183-34-3 ]
  • [ 1000801-75-1 ]
YieldReaction ConditionsOperation in experiment
84.9% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 85℃; for 24 h; Inert atmosphere A mixture of potassium acetate (1.56 g, 15.91 mmol) , Pd (dppf) Cl2 (190 mg, 0.27 mmol) , 1- (cyclopropylmethyl) -4-iodo-1H-pyrazole (1.31 g, 5.30 mmol) and bis (pinacolato) diboron (1.62 g, 6.36 mmol) in DMF (25.00 mL) was stirred at 85 under N2 for 24 h and cooled to rt, and then filtered through a Celite pad. The filtrate was diluted with water (50 mL) , and then extracted with EtOAc (50 mL × 3) . The combined organic layers were concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with PE/EtOAc (v/v) 3/1 to give a yellow oily product (1.11 g, 84.9) .[1449]MS (ESI, pos. ion) m/z: 249.1 [M+1] +
Reference: [1] Patent: WO2016/615, 2016, A1, . Location in patent: Paragraph 00642
  • 6
  • [ 1216152-26-9 ]
  • [ 73183-34-3 ]
  • [ 1000801-75-1 ]
YieldReaction ConditionsOperation in experiment
0.15 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 12 h; Inert atmosphere; Sealed tube b) 1 -(Cyclopropylmethyl)-4-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)- 1 H- pyrazoleTo a degassed (N2 bubbling) solution of the compound of Intermediate Example 9(a) (0.15 g, 0.75 mmol) in 1,4-dioxane (10 ml) were added 4,4,4*,4',5,5,5',5'-octa- methyl-2,2'-bi(l,3,2-dioxaborolane) (0.23 g, 0.9 mmol, 1.2 eq.), Pd(dppf Cl2 (0.12 g, 0.15 mmol, 0.2 eq.) and potassium acetate (0.25 g, 2.55 mmol, 3.4 eq.). using the procedure of Intermediate Example 1(b). The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica gel, 30 percent ethyl acetate in hexane) to give the product in 81 percent yield (0.15 g). LC-MS (ESI):Calculated mass: 248.13; Observed mass: 249.2 [(M+H]+ (rt: 1.58 min).
0.15 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 12 h; Sealed tube; Inert atmosphere To a degassed (N2 bubbling) solution of the compound of Intermediate Example 9(a) (0.15 g, 0.75 mmol) in 1,4-dioxane (10 ml) were added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (0.23 g, 0.9 mmol, 1.2 eq.), Pd(dppf)Cl2 (0.12 g, 0.15 mmol, 0.2 eq.) and potassium acetate (0.25 g, 2.55 mmol, 3.4 eq.).
using the procedure of Intermediate Example 1(b).
The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica gel, 30percent ethyl acetate in hexane) to give the product in 81percent yield (0.15 g). LC-MS (ESI): Calculated mass: 248.13; Observed mass: 249.2 [(M+H]+ (rt: 1.58 min).
Reference: [1] Patent: WO2013/53983, 2013, A1, . Location in patent: Page/Page column 33; 34
[2] Patent: US2015/11548, 2015, A1, . Location in patent: Paragraph 0143
  • 7
  • [ 2924-09-6 ]
  • [ 73183-34-3 ]
  • [ 1003575-43-6 ]
YieldReaction ConditionsOperation in experiment
100% With potassium acetate In N,N-dimethyl-formamide at 100℃; for 2 h; Inert atmosphere A vial was charged with 5-bromo-2-fluoroaniline (1 g, 5.26 mmol), bis(pinacolato)diboron (1.6 g , 6.31 mmol), potassium acetate (1.03 g, 10.52 mmol), Pd(dppf)Cl2 * CH2C12 (129 mg, 0.158 mmol), and DMF (10 mL) under nitrogenatmosphere. After stirring for 2 h at 100 °C the reaction mixture was concentrated in vacuo, the residue was triturated with EtOAc and filtered through a pad of celite. The filtrate was adsorbed on silica gel. Purification by flash silica gel chromatography using a gradient of 0- 30percent EtOAc/hexane afforded 1.25 g of pinacol 3-amino-4-fluoroboronate as a light yellow oil (quant.): 1H NMR (CDC13, ppm) δ 1.36 (s, 12H), 3.71 (broad s, 2H), 7.00 (dd, 1H), 7.19 (m, 1H), 7.26 (dd, 1H); [M+H]+ m/z 238.
Reference: [1] Patent: WO2012/125981, 2012, A2, . Location in patent: Page/Page column 128
  • 8
  • [ 2106-05-0 ]
  • [ 73183-34-3 ]
  • [ 1003575-43-6 ]
YieldReaction ConditionsOperation in experiment
81% With (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride; dichlorobis(trimethylphosphine)nickel In tetrahydrofuran at 100℃; for 12 h; Inert atmosphere; Sealed tube Under an argon atmosphere,4.2 mg (0.015 mmol) of dichlorobis (trimethylphosphine) nickel,72.8 mg (0.5 mmol) of 5-chloro-2-fluoroaniline,152 mg (1.0 mmol) of cesium fluoride,140 mg (0.55 mmol) of 4,4,5,5,4 ', 4', 5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolanyl)180 mg (1.05 mmol) of trimethyl (2,2,2-trifluoroethoxy) silane and 0.5 mL of tetrahydrofuran were added and sealed,And the mixture was stirred at 100 ° C. for 12 hours.After the reaction vessel was cooled to room temperature, 1 mL of a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted three times with 8 mL of ethyl acetate, and the obtained organic phases were combined.The solvent was distilled off under reduced pressure, and the residue was purified using silica gel column chromatography (hexane: chloroform: ethyl acetate = 4: 1: 0 to 4: 1: 1)96 mg (pale yellow liquid, yield 81percent) of 2-fluoro-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline was obtained
Reference: [1] Organic Letters, 2011, vol. 13, # 21, p. 5766 - 5769
[2] Patent: JP5699037, 2015, B2, . Location in patent: Paragraph 0105; 0106
  • 9
  • [ 81971-39-3 ]
  • [ 73183-34-3 ]
  • [ 1002309-52-5 ]
YieldReaction ConditionsOperation in experiment
23.6% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 2 h; Microwave irradiation A solution of 5-bromo-1-methylpyridin-2-one (200.0 mg, 1.06 mmol), bis(pinacolato)diboron (410.0 mg, 1.61 mmol), potassium acetate (270 mg, 2.67 mmol), Pd (dppf)Cl2 (80 mg, 0.11 mmol) in dioxane (5 mL) was heated at 100° C. for 2 h under microwave.
The mixture was filtered, washed with water and extracted with ethyl acetate (20 mL*3).
The combined organics were dried over Na2SO4, filtered and concentrated to give the crude title compound (59.0 mg, 23.6percent). LCMS (M+H)+ 236.
160 mg With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In ethylene glycol at 80℃; for 3 h; To a stirred suspension of 5-bromo-l-methylpyridin-2(lH)-one (470 mg, 2.49 mmol), potassium acetate (736 mg, 7.49 mmol) and bis(pinacolato)diboron (952 mg, 3.74 mmol) in degassed polyethylene glycol-400 (15 mL) was added [1, 1 '- bis(diphenylphosphino)ferrocene]dichloropalladium (II) (204 mg, 0.24 mmol) at RT. The resultant suspension was stirred for 3 h at 80 °C. The reaction mixture was cooled to RT, diluted with ethyl acetate (100 mL) and washed with water (100 mL) followed by brine (100 mL). The organic layer was concentrated and the residue obtained purified by flash column chromatography to afford 160 mg of the titled product; 1H NMR (300 MHz, CDC13) δ 1.30 (s, 12H), 3.54 (s, 3H), 6.53 (d, J = 9.3 Hz, 1H), 7.60 (d, J = 9.0 Hz, 1H), 7.75 (s, 1H); APCI- MS (m/z) 236 (M+H)+.
Reference: [1] Patent: US2015/111885, 2015, A1, . Location in patent: Paragraph 0574; 0575
[2] Patent: EP2168965, 2010, A1, . Location in patent: Page/Page column 33
[3] Patent: WO2008/8539, 2008, A2, . Location in patent: Page/Page column 117-118
[4] Patent: WO2012/3189, 2012, A1, . Location in patent: Page/Page column 81
[5] Patent: WO2011/60235, 2011, A1, . Location in patent: Page/Page column 22
[6] Patent: WO2015/75665, 2015, A1, . Location in patent: Page/Page column 85; 108
[7] Patent: WO2017/21879, 2017, A1, . Location in patent: Page/Page column 64
[8] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 17, p. 2993 - 2997
  • 10
  • [ 73183-34-3 ]
  • [ 1002309-52-5 ]
YieldReaction ConditionsOperation in experiment
64% With tris-(dibenzylideneacetone)dipalladium(0); potassium hydroxide; tricyclohexylphosphine In 1,4-dioxane at 80℃; for 5 h; Inert atmosphere To a mixture of 5-bromo-1-methylpyridin-2(1H)-one (1.0 g, 5.32 mmol), KOH (0.78 g, 7.98 mmol) and bis(pinacolato)diboron (0.162 g, 6.38 mmol) in 1 ,4-dioxane (20 mL), tricyclohexyiphosphine (149 mg, 0.532 mmol), Pd2dba3 (487 mg, 0.532 mmol) were added under N2 atmosphere. The mixture was stirred at about 80 °C for about 5 h. Then water was added, the aqueous layer was extracted with EtOAc (50 mL x 2), and the organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure and the residue was purified by column chromatograph on silica gel to provide ]-methyl-5-(4, 4,5, 5-tetramethyl-], 3, 2-dioxaborolan-2-yl)pyridin-2(]H)-one (0.80 g, 64percent): ‘H NMR (CDC13) 7.70 (s, 1 H), 7.54 (d, J= 8.8 Hz, 1 H), 6.47 (d, J= 8.8 Hz, 1 H), 3.49 (s, 3 H), 1.24(s, 12 H).
Reference: [1] Patent: WO2014/210255, 2014, A1, . Location in patent: Page/Page column 100
  • 11
  • [ 694-85-9 ]
  • [ 73183-34-3 ]
  • [ 1002309-52-5 ]
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 21, p. 4745 - 4752
  • 12
  • [ 694-85-9 ]
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  • [ 1002309-52-5 ]
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 21, p. 4745 - 4752
[2] Synthesis (Germany), 2017, vol. 49, # 21, p. 4745 - 4752
  • 13
  • [ 73183-34-3 ]
  • [ 1003846-21-6 ]
YieldReaction ConditionsOperation in experiment
280 g With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; for 12 h; Inert atmosphere Step 2.
Bis(pinacolato)diboron (247 g, 0.974 mol, 1.5 eq) was added to a solution of 4-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole (150 g, 0.65 mol, 1.0 eq) in 1,4-dioxane (1500 ml) at room temperature.
Potassium acetate (127 g, 1.30 mol, 2 eq) was then added and the reaction flask was purged with argon for 20 min. PdCl2(dppf) DCM (26.0 g, 31.8 mmol, 0.05 eq) was added and the mixture was purged with argon for further 10 min followed by stirring at 80° C. for 12 h.
After completion of the reaction (monitored by TLC, 10percent ethyl acetate-hexane Rf=0.3), the mixture was cooled to room temperature and filtered through a bed of diatomaceous earth.
The bed of diatomaceous earth was washed with ethyl acetate and the combined organic layers were evaporated under reduced pressure to give 1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (280 g crude) as a brown oil. LCMS purity: 57.8percent; (ES+): m/z 279.18 (M+H+); tr=1.95 min.
The compound was used without further purification.
Reference: [1] Patent: US2015/252051, 2015, A1, . Location in patent: Paragraph 0165; 0167
[2] Patent: US2015/252022, 2015, A1, . Location in patent: Paragraph 0207; 0209
[3] Patent: WO2016/14913, 2016, A1, . Location in patent: Paragraph 109
[4] Patent: WO2016/14916, 2016, A1, . Location in patent: Paragraph 109
[5] Patent: WO2016/14918, 2016, A1, . Location in patent: Paragraph 107
[6] Patent: US2017/298060, 2017, A1, . Location in patent: Paragraph 0082; 0084
[7] Patent: US2016/24056, 2016, A1, . Location in patent: Paragraph 0201
  • 14
  • [ 1040377-02-3 ]
  • [ 73183-34-3 ]
  • [ 1003846-21-6 ]
Reference: [1] Patent: WO2014/86032, 2014, A1, . Location in patent: Page/Page column 43
  • 15
  • [ 675109-26-9 ]
  • [ 73183-34-3 ]
  • [ 1004294-80-7 ]
YieldReaction ConditionsOperation in experiment
82% With potassium acetate In 1,4-dioxane at 70 - 120℃; for 18 h; To a solution of 6-bromo-2,3-dihydro-isoindol-l-one (1 equiv) in dry dioxan (0.1 M) were added bis(pinacolato)diboron (1.1 equiv), potassium acetate (3.5 equiv) and dppf (0.05 equiv). The reaction mixture was degassed with nitrogen for 20 minutes. PdCl2(dppf) (0.05 equiv) was added to the reaction mixture, which was degassed for a further 5 minutes. The reaction mixture was heated to 70°C for 2 hours under nitrogen then heated to 1200C for 16 hours. The reaction mixture was partitioned between EtOAc and water. The aqueous phase was further extracted with EtOAc and the combined organic phases dried (MgSO4), filtered and concentrated in vacuo. The residue was sonicated in EtOAc, the suspension was filtered onto a sintered funnel and the collected grey solid was dried and used without further purification. 6-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-l-one: (82 percent yield, 29 percent purity, main impurity being the boronic acid 43 percent) m/z (LC-MS, ESP): 519.5 [2M+H]+ R/T = 3.38 min
Reference: [1] Patent: WO2008/23161, 2008, A1, . Location in patent: Page/Page column 117
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9542 - 9555
[3] Patent: WO2017/107089, 2017, A1, . Location in patent: Page/Page column 37; 38
[4] Patent: WO2017/68412, 2017, A1, . Location in patent: Page/Page column 208; 209
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 11, p. 4978 - 4992
  • 16
  • [ 73183-34-3 ]
  • [ 1004294-80-7 ]
Reference: [1] Patent: WO2015/189744, 2015, A1,
  • 17
  • [ 67927-44-0 ]
  • [ 73183-34-3 ]
  • [ 1016641-53-4 ]
YieldReaction ConditionsOperation in experiment
81% With potassium acetate In 1,4-dioxane at 100℃; for 7 h; A mixture of compound B2.2 (1 equiv., 17 mmol, 3.8 g), bis(pinacolato)diboron (1.1 equiv., 18 mmol, 4.7 g), potassium acetate (2 equiv., 33 mmol, 3.3 g) and trans- dichlorobis(triphenylphoshpine) palladium(II) (0.03 equiv., 0.5 mmol, 0.41 g) in dioxane (180 ml) was stirred at 1000C under Ar for 7 h. Water was added and the aqueous layer was extracted with dichloromethane. The organic layer was dried with MgSO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluens: dichloromethane) to give a white powder B2.3(3.7 g, yield = 81percent, purity (LC) = 81percent).
Reference: [1] Patent: WO2008/37784, 2008, A1, . Location in patent: Page/Page column 35; 36
[2] Patent: US2016/9720, 2016, A1, . Location in patent: Paragraph 0439
[3] Patent: US2016/9712, 2016, A1, . Location in patent: Paragraph 0361
[4] Patent: US2016/289238, 2016, A1, . Location in patent: Paragraph 0324; 0325
  • 18
  • [ 73183-34-3 ]
  • [ 623-47-2 ]
  • [ 1009307-13-4 ]
YieldReaction ConditionsOperation in experiment
65% With methanol; [5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphane; copper(l) chloride; sodium t-butanolate In tetrahydrofuran at 20℃; for 24 h; Inert atmosphere General procedure: CuCl (1.5 mg, 0.015 mmol), NaOt-Bu (2.9 mg, 0.03 mmol), and Xantphos ligand (8.7 mg, 0.015 mmol) were placed in an oven-dried Schlenk tube under nitrogen and THF (0.45 mL) were added. The reaction mixture was stirred for 30 min at room temperature and then bis(pinacolato)diboron (127 mg, 0.5 mmol) in THF (0.3 mL) was added. The reaction mixture was stirred for 10 min and α,β-acetylenic ester 2 (0.5 mmol) was added, followed by MeOH (40 μL, 1 mmol). The reaction tube was washed with further THF (0.2 mL), sealed, and stirred until no starting material was detected by TLC. The reaction mixture was filtered through a pad of Celite and concentrated. The product was purified by silica gel chromatography.
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 20, p. 8903 - 8925,23
[2] Organic and Biomolecular Chemistry, 2015, vol. 13, # 26, p. 7136 - 7139
[3] New Journal of Chemistry, 2018, vol. 42, # 21, p. 17346 - 17350
[4] Chemical Communications, 2008, # 6, p. 733 - 734
[5] Tetrahedron, 2012, vol. 68, # 17, p. 3444 - 3449
[6] Organic Letters, 2010, vol. 12, # 5, p. 1024 - 1027
  • 19
  • [ 15115-52-3 ]
  • [ 73183-34-3 ]
  • [ 1002334-12-4 ]
YieldReaction ConditionsOperation in experiment
50% With potassium acetate In dimethyl sulfoxide at 20 - 80℃; To a solution of compound 4-bromo-l -phenyl- lH-pyrazo Ie (0.5 g, 2.3 mmol) in DMSO (50 mL) was added KOAc (0.66 g, 6.8 mmol), bis(pinacolato)diboron (0.63 g, 2.5 mmol) and .yen.dCb(dpp{) (0.076g, 0.11 mmol) at room temperature. The reaction mixture was stirred overnight at 8O0C. The result mixture was diluted with EA, washed with brine, dried over Na2SO4, concentrated, purified by chromatography (EA:PE=1: 12) to give l-phenyl-4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-lH- pyrazole (0.3 g, 50percent) as light yellow solid
Reference: [1] Patent: WO2009/155527, 2009, A2, . Location in patent: Page/Page column 134
  • 20
  • [ 23889-85-2 ]
  • [ 73183-34-3 ]
  • [ 1002334-12-4 ]
YieldReaction ConditionsOperation in experiment
48.15% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 8 h; Inert atmosphere A mixture of 4-iodo-1-phenyl-1H-pyrazole (706 mg, 2.59 mmol) , potassium acetate (762 mg, 7.76 mmol) , bis (pinacolato) diboron (860 mg, 3.37 mmol) and Pd (dppf) Cl2(212 mg, 0.26 mmol) was suspended in DMSO (15 mL) . The system was exchanged with N2. The mixture was stirred at 80 for 8 h. The reaction mixture was diluted with water (60 mL) . The resulting mixture was extracted with DCM (50 mL × 3) . The combined organic layers were washed with saturated aqueous NaCl (15 mL) , dried over anhydrous Na2SO4and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with PE/EtOAc (v/v) 20/1 to give a yellow solid product (340 mg, 48.15) .[1650]MS (ESI, pos. ion) m/z: 271.05 [M+1]+.
Reference: [1] Patent: WO2016/615, 2016, A1, . Location in patent: Paragraph 00690
  • 21
  • [ 73183-34-3 ]
  • [ 38749-79-0 ]
  • [ 1012084-56-8 ]
Reference: [1] Patent: US2009/143361, 2009, A1, . Location in patent: Page/Page column 52
[2] Patent: US2009/143367, 2009, A1, . Location in patent: Page/Page column 37
[3] Patent: US2010/120763, 2010, A1, . Location in patent: Page/Page column 47
[4] European Journal of Organic Chemistry, 2012, # 3, p. 595 - 603
  • 22
  • [ 942590-05-8 ]
  • [ 73183-34-3 ]
  • [ 1021918-86-4 ]
YieldReaction ConditionsOperation in experiment
42% With potassium acetate; triethylamine In 1,4-dioxane at 110℃; A mixture of 1 , 1 -dimethylethyl 5-bromo-lH-benzimidazole-l -carboxylate (10.2 mmol), bis(pinacolato)diboron (11.2 mmol), palladium(II) acetate (1.02 mmol), dichloro[l,l '-bis(diphenylphosphino)ferrocene]palladium(II) (1.02 mmol), and potassium acetate (30.4 mmol) in triethylamine (2 mL) and 1,4-dioxane (50 mL) was heated at 110 °C overnight. The reaction mixture was concentrated in vacuo and the residue purified by flash chromatography (10percent ethyl acetate/petroleum ether) to afford the title product as a solid (42percent).
1.47 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium diacetate; triethylamine In 1,4-dioxane at 110℃; Inert atmosphere 1 ,1 -Dimethylethyl 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-benzimidazole-1 - carboxylateTo a solution of 1 , 1 -dimethylethyl 5-bromo-1 /-/-benzimidazole-1 -carboxylate (3.02 g) in 1 ,4- dioxane (50 mL) were added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1 ,3,2-dioxaborolane (2.837 g), potassium acetate (7.978 g) and TEA (2 mL). Pd(OAc)2 (227 mg) and Pd(dppf)CI2 (743 mg) were added under nitrogen and the reaction mixture was stirred under reflux (1 10 °C) overnight. The reaction mixture was washed with water three times and with saturated brine and dried over sodium sulfate. Solvent was removed under reduced pressure and the crude product was purified by silica gel column chromatography (petroleum ether / EtOAc 8:1 ) to afford 1.47 g of the titled compound.
Reference: [1] Patent: WO2011/66211, 2011, A1, . Location in patent: Page/Page column 71
[2] Patent: WO2009/7751, 2009, A2, . Location in patent: Page/Page column 120-121
[3] Patent: WO2008/51493, 2008, A2, . Location in patent: Page/Page column 151
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 22, p. 6793 - 6799
[5] Patent: WO2013/28445, 2013, A1, . Location in patent: Page/Page column 56; 57
  • 23
  • [ 73183-34-3 ]
  • [ 1021918-86-4 ]
Reference: [1] Patent: CN105254613, 2016, A, . Location in patent: Paragraph 0107; 0108; 0109
  • 24
  • [ 1024120-52-2 ]
  • [ 73183-34-3 ]
  • [ 1029716-44-6 ]
YieldReaction ConditionsOperation in experiment
68.5% With potassium acetate In 1,4-dioxane at 50℃; for 16 h; Inert atmosphere 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (11-II)To a solution of compound 11-II-a (600 mg, 2.73 mmol) in dioxane (15 mL) was added KOAc (800 mg, 8.2 mmol), bis(pinacolato)diboran (1.39 g, 5.4 mmol) and Pd(dppf)Cl2 (0.06 g, 0.08 mmol) at RT. The reaction mixture was degassed by purging with argon for 30 minutes and stirred at 50° C. for 16 h. After completion of the reaction (monitored by TLC), the reaction was quenched with H2O and extracted with EtOAc (3.x.100 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The crude compound was purified by column chromatography (15percent EtOAc/Hexane) to afford 11-II (500 mg, 68.5percent) as off white solid. TLC: 30percent EtOAc/Hexane (Rf: 0.4); 1H-NMR (CDCl3, 200 MHz): δ 7.90 (s, 1H), 7.79 (s, 1H), 5.56 (q, J=6.0 Hz, 1H), 3.55-3.25 (m, 2H), 1.63 (d, J=6.0 Hz, 3H), 1.35 (s, 12H), 1.15 (t, J=7.2 Hz, 3H); Mass: 267 [M++1].
68.5% With potassium acetate In 1,4-dioxane 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (5-II)
To a solution of compound 5-II-a (600 mg, 2.73 mmol) in dioxane (15 mL) was added KOAc (800 mg, 8.2 mmol), bis(pinacolato)diboran (1.39 g, 5.4 mmol) and Pd(dppf)Cl2 (0.06 g, 0.08 mmol) at RT.
The reaction mixture was degassed by purging with argon for 30 minutes and stirred at 50° C. for 16 h.
After completion of the reaction (monitored by TLC), the reaction was quenched with H2O and extracted with EtOAc (3*100 mL).
The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo.
The crude compound was purified by column chromatography (15percent EtOAc/Hexane) to afford 5-II (500 mg, 68.5percent) as off white solid. TLC: 30percent EtOAc/Hexane (Rf: 0.4); 1H-NMR (CDCl3, 200 MHz): δ 7.90 (s, 1H), 7.79 (s, 1H), 5.56 (q, J=6.0 Hz, 1H), 3.55-3.25 (m, 2H), 1.63 (d, J=6.0 Hz, 3H), 1.35 (s, 12H), 1.15 (t, J=7.2 Hz, 3H); Mass: 267 [M++1].
Reference: [1] Patent: US2011/230476, 2011, A1, . Location in patent: Page/Page column 293
[2] Patent: US2011/269244, 2011, A1, . Location in patent: Page/Page column
  • 25
  • [ 73183-34-3 ]
  • [ 575452-22-1 ]
  • [ 1029716-44-6 ]
Reference: [1] Patent: WO2016/90285, 2016, A1, . Location in patent: Paragraph 00367
  • 26
  • [ 1040377-07-8 ]
  • [ 73183-34-3 ]
  • [ 1029715-63-6 ]
YieldReaction ConditionsOperation in experiment
65.6%
Stage #1: With potassium acetate In N,N-dimethyl-formamide for 0.166667 h;
Stage #2: at 80℃;
To a solution of 21c (0.79g, 3.64mmol) and bis(pinacolato)diboron (1.1 Ig, 4.37mmol) in DMF (2OmL), was added KOAc (1.07g, 10.92mmol). The mixture was 25 degassed with N2 and stirred for lOmin, then was added Pd(dppf)Cl2 (89mg, 0.109mmol). The resulting mixture was degassed with N2 and stirred at 800C overnight. After the reaction was complete, DMF was evaporated and the residue was purified by column chromatography (EA:PE=1 : 10) to afford 21d (0.63g, 65.6percent yield).
Reference: [1] Patent: WO2008/88881, 2008, A1, . Location in patent: Page/Page column 46
  • 27
  • [ 110-87-2 ]
  • [ 73183-34-3 ]
  • [ 1046811-99-7 ]
  • [ 1025707-93-0 ]
Reference: [1] Chemistry Letters, 2008, vol. 37, # 6, p. 664 - 665
[2] Chemistry Letters, 2008, vol. 37, # 6, p. 664 - 665
[3] Bulletin of the Chemical Society of Japan, 2008, vol. 81, # 12, p. 1535 - 1553
  • 28
  • [ 73183-34-3 ]
  • [ 1022092-33-6 ]
YieldReaction ConditionsOperation in experiment
36% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 115℃; Inert atmosphere To a mixture of 3- (4-bromo-1H-pyrazol-1-yl) propanenitrile (20.00 mmol, 4.00 g) , bis (pinacolato) diboron (6.00 g, 23.63 mmol) , Pd (dppf) Cl2(0.74 g, 1.00 mmol) and potassium acetate (4.00 g, 39.53 mmol) was added 1, 4-dioxane (40 mL) via syringe under N2. The mixture was stirred at 115 overnight. The mixture was cooled to rt and filtered through a Celite pad. The filter cake was washed with DCM. The combined filtrates were dried over anhydrous Na2SO4and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with PE/EtOAc (v/v) 2/1 to give a light yellow oily product (1.80 g, 36.0, containing bis (pinacolato) diboron) .[0848]MS (ESI, pos. ion) m/z: 248.1 [M+1]+ and[0849]1H NMR (600 MHz, DMSO-d6) : δ (ppm) 8.03 (s, 1H) , 7.80 (d, J 2.2 Hz, 1H) , 7.66 (s, 1H) , 7.51 (d, J 1.6 Hz, 1H) , 6.28 (t, J 2.0 Hz, 1H) , 4.40 (dt, J1 9.5 Hz, J2 6.4 Hz, 4H) , 3.06 (dt, J1 13.0 Hz, J2 6.4 Hz, 4H) , 1.26 (s, 12H)
Reference: [1] Patent: WO2016/615, 2016, A1, . Location in patent: Paragraph 00500
  • 29
  • [ 39795-60-3 ]
  • [ 73183-34-3 ]
  • [ 1009033-87-7 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With potassium acetate In 1,4-dioxane for 0.5 h; Inert atmosphere; Sealed tube
Stage #2: at 100℃;
A 100 mL sealed tube was charged with 4-(4-bromophenyl)pyridine (0.9 g, 3.8mmol), bis(pinacolato)diboron (1.17 g, 4.61 mmol), potassium acetate (0.745 g, 7.6mmol) and 1-4 dioxane (10 mL). The reaction mixture was purged with argon for 30mm. Then, Pd(dppf)C12 (0.75 g, 0.05 eq) was added and heated at 100 00 over night.After cooing, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous Na2SO4. The organic layer was concentrated under vacuo to yield crude product, which was purified by combif lash to yield title compound (1.0 g, 100.0percent). LCMS: (M+H) = 282.1
Reference: [1] Patent: WO2014/202528, 2014, A1, . Location in patent: Page/Page column 104
[2] Organic Letters, 2008, vol. 10, # 5, p. 941 - 944
  • 30
  • [ 183065-68-1 ]
  • [ 73183-34-3 ]
  • [ 1008119-07-0 ]
YieldReaction ConditionsOperation in experiment
19% With potassium acetate In 1,4-dioxane at 80℃; for 21 h; A dioxane (16.5 mL) solution of 4-bromo-2,6-difluorobenzoic acid (0.4 g, 1.6 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (0.5 g, 2.0 mmol), PdCl2(dppf) (0.12 g, 0.17 mmol) and potassium acetate (0.49 g, 4.9 mmol) was placed in a sealed vial and degassed by vacuum-N2 refill cycle twice. The mixture was heated to 80° C. for 21 h, cooled to room temperature and filtered through a short bed of silica gel. The filtrate was concentrated and purified by flash column chromatography (ISCO 12 g silica gel cartridge, 20-100percent ethyl acetate-hexanes) to give the expected product as a brown oil (0.11 g, 19percent). MS (ES-) m/z: 283 (M-H); LC retention time: 1.48 min (Analytical HPLC Method D).
Reference: [1] Patent: US2009/75995, 2009, A1, . Location in patent: Page/Page column 67
  • 31
  • [ 67856-45-5 ]
  • [ 73183-34-3 ]
  • [ 1002727-88-9 ]
YieldReaction ConditionsOperation in experiment
84% With potassium acetate In N,N-dimethyl-formamide at 95℃; for 5.16667 h; Step 3:A solution of the 6-iodochroman 11c (1.0 g, 3.85 mmol), bis[pinocolato]diborane (1.22 g, 4.81 mmol) and potassium acetate (1.1O g, 11.5 mmol) in DMF (36 mL) is degassed with Ar for 5 min followed by the addition of the PdCI2dppf-DCM complex (314 mg, 0.38 mmol). The reaction mixture is then degassed for an additional 5 min before being heated to 950C for 5 h. The reaction is then cooled to RT. The crude reaction mixture is diluted with water and the product is extracted 3 times with EtOAc (3 x 100 mL). The combined organics are washed with water (100 mL) and brine (100 mL). The organic phase is then dried over MgSO4 and filtered and concentrated. The crude mixture is further purified by CombiFlash.(R). Companion using a gradient of EtOAc/hexanes to afford the borane fragment 11d (840 mg, 84percent yield).
84% With potassium acetate In N,N-dimethyl-formamide at 95℃; for 5.16 h; A solution of the 6-iodochroman 11c (1.O g, 3.85 mmol), bis[pinocolato]diborane (1.22 g, 4.81 mmol) and potassium acetate (1.1O g, 11.5 mmol) in DMF (36 mL) is degassed with Ar for about 5 min followed by the addition of the PdCI2dppf-DCM complex (314 mg, 0.38 mmol). The reaction mixture is then degassed for about an additional 5 min before being heated to 950C for about 5 h. The reaction is then cooled to RT. The crude reaction mixture is diluted with water and the product is extracted 3 times with EtOAc (3 x 100 mL). The combined organics are washed with water (100 mL) and brine (100 mL). The organic phase is then dried over MgSO4 and filtered and concentrated. The crude mixture is further purified by CombiFlash.(R). Companion using a gradient of EtOAc/hexanes to afford the borane fragment 11d (840 mg, 84percent yield).
84%
Stage #1: With potassium acetate In N,N-dimethyl-formamide for 0.0833333 h;
Stage #2: at 95℃; for 5.08 h;
A solution of the 6-ιodochroman 11c (1 0 g, 3 85 mmol), bιs[pιnocolato]dιborane (1 22 g, 4 81 mmol) and potassium acetate (1 10 g, 11 5 mmol) in DMF (36 mL) is degassed with Ar for 5 mm followed by the addition of the PdCI2dppf-DCM complex (314 mg, 0 38 mmol) The reaction mixture is then degassed for an additional 5 mm before being heated to 950C for 5 h The reaction is then cooled to RT The crude reaction mixture is diluted with water and the product is extracted with EtOAc (3 x 100 mL) The combined organics are washed with water (100 mL) and brine (100 mL) The organic phase is then dried over MgSO4 and filtered and concentrated The crude mixture is further purified by CombiFlash.(R). Companion using a gradient of EtOAc/hexanes to afford the borane fragment 11d (840 mg, 84percent yield)
Reference: [1] Patent: WO2009/62285, 2009, A1, . Location in patent: Page/Page column 66-67
[2] Patent: WO2009/62308, 2009, A1, . Location in patent: Page/Page column 76
[3] Patent: WO2009/62288, 2009, A1, . Location in patent: Page/Page column 72-73
  • 32
  • [ 493-08-3 ]
  • [ 73183-34-3 ]
  • [ 1002727-88-9 ]
YieldReaction ConditionsOperation in experiment
84% With potassium acetate In N,N-dimethyl-formamide at 95℃; for 5 h; A solution of the 6-iodochroman 11c (1.0 g, 3.85 mmol), bis[pinocolato]diborane (1.22 g, 4.81 mmol) and potassium acetate (1.1O g, 11.5 mmol) in DMF (36 mL) is degassed with Ar for 5 min followed by the addition of the PdCI2dppf-DCM complex (314 mg, 0.38 mmol). The reaction mixture is then degassed for an additional 5 min before being heated to 950C for 5 h. The reaction is then cooled to RT. The crude reaction mixture is diluted with water and the product is extracted with EtOAc (3 x 100 mL). The combined organics are washed with water (100 mL) and brine (100 mL). The organic phase is then dried over MgSO4 and filtered and concentrated. The crude mixture is further purified by CombiFlash.(R). Companion using a gradient of EtOAc/hexanes to afford the borane fragment 11d (840 mg, 84percent yield).
Reference: [1] Patent: WO2009/62289, 2009, A1, . Location in patent: Page/Page column 79; 80
  • 33
  • [ 3875-78-3 ]
  • [ 73183-34-3 ]
  • [ 1002727-88-9 ]
YieldReaction ConditionsOperation in experiment
59% With potassium acetate In N,N-dimethyl-formamide at 95℃; for 3 h; Inert atmosphere Step 1. 2-(Chroman-6-yl)-4,4,5,5-tetramethyl-l ,3,2-dioxaborolaneTo a solution of 6-bromochroman (400 mg, 1.88 mmol) in N,N-dimethylformamide (50 mL) was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (620 mg, 2.44 mmol), KOAc (552.1 mg, 5.63 mmol) and Pd(dppf)Cl2 (155 mg, 0.19 mmol) with stirring for 3 h at 95°C maintained with an inert atmosphere of nitrogen in an oil bath. The reaction mixture was diluted with water, extracted with ethyl acetate (80 mL x 3) and the organic layers combined, dried over anhydrous magnesium sulfate, concentrated under vacuum to give the residue, which was applied onto a silica gel column with 1 percent ethyl acetate in petroleum ether to afford 2-(chroman-6-yl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane as colorless oil (320 mg, 59percent).*H-NMR (300 MHz, CDC13): δ 7.54 (d, J = 7.5 Hz, 2H), 6.78 (d, J = 8.4 Hz, 1H), 4.19 - 4.23 (t, J = 5.4 Hz, 2H), 2.78 - 2.83 (t, J = 6.3 Hz, 2H), 1.98 - 2.05 (m, 2H), 1.28 (s,12H)
Reference: [1] Patent: WO2012/119046, 2012, A2, . Location in patent: Page/Page column 72
  • 34
  • [ 625-92-3 ]
  • [ 73183-34-3 ]
  • [ 1012085-50-5 ]
Reference: [1] Journal of Natural Products, 2017, vol. 80, # 4, p. 1205 - 1209
[2] Patent: US2010/174086, 2010, A1, . Location in patent: Page/Page column 10-11
[3] Patent: WO2010/80471, 2010, A1, . Location in patent: Page/Page column 19
[4] Patent: WO2010/80471, 2010, A1, . Location in patent: Page/Page column 23-24
  • 35
  • [ 110-86-1 ]
  • [ 73183-34-3 ]
  • [ 1012085-50-5 ]
  • [ 181219-01-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 17, p. 4853 - 4857[2] Angew. Chem., 2017, vol. 129, # 17, p. 4931 - 4935,5
  • 36
  • [ 1183903-41-4 ]
  • [ 73183-34-3 ]
  • [ 1000801-76-2 ]
YieldReaction ConditionsOperation in experiment
51% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 100℃; for 13 h; Inert atmosphere To a solution of 4-bromo-1- (3-methoxypropyl) -1H-pyrazole (2.1 g, 9.6 mmol) in DMSO (20 mL) were added bis (pinacolato) diboron (3.7 g, 15 mmol) , potassium acetate (2.4 g, 24 mmol) and Pd (dppf) Cl2(900 mg, 1.22 mmol) . The mixture was stirred at 100 under N2for 13 h, cooled to rt and quenched with saturated aqueous NaCl (30 mL) . The resulting mixture was extracted with DCM (30 mL × 3) . The combinded orgainc layers were dried over anhydrous Na2SO4and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with PE/EtOAc (v/v) 2/1 to give a light yellow oily product (1.3 g, 51) .[1271]MS (ESI, pos. ion) m/z: 267.0 [M+1]+
Reference: [1] Patent: WO2016/615, 2016, A1, . Location in patent: Paragraph 00598
[2] Patent: WO2010/129848, 2010, A2, . Location in patent: Page/Page column 24-25
  • 37
  • [ 6358-77-6 ]
  • [ 73183-34-3 ]
  • [ 1000339-10-5 ]
YieldReaction ConditionsOperation in experiment
80% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 8 h; Inert atmosphere Synthesis of 2-methoxy-5-(4, 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 28.12
To potassium acetate (8.9 g, 90.83 mmol), bis-(pinacolato)-diboron (8.1 g, 31.86 mmol) and bis(diphenylphosphine) ferrocene dichloropalladium (II) (0.34 g, 0.48 mmol) was added an anhydrous solution of 5-bromo-2-methoxyaniline (3.22 g, 15.93 mmol) in DMSO (40 mL) under anhydrous conditions in an atmosphere of nitrogen.
The mixture was stirred at 80° C. for 8 h after which time the reaction was quenched with saturated NaCl aqueous solution (30 mL) and extracted with diethyl ether (3*20 mL).
The combined ether extracts were dried over magnesium sulphate, filtered and concentrated.
The crude product was purified by flash column chromatography (stationary phase; silica gel 230-400 mesh, mobile phase; 9:1 hexane/ethyl acetate).
All homogenous fractions were collected and reduced in volume to afford the product 28.12 as a brown syrup (3.18 g, 80percent).
νmax (DCM)/cm-1: 2926.38, 1599.02, 1431.11, 1356.01, 1221.39, 1142.48
1H NMR (CDCl3, 400 MHz) δH ppm: 1.35 (12H, s, 2*C(CH3)2), 3.89 (3H, s, OCH3), 6.15 (2H, br, NH2), 7.18 (1H, d, J 8.0 Hz, ArH), 7.25 (1H, d, J 2.5 Hz, ArH), 7.29 (1H, s, ArH).
13C NMR δc ppm: 24.5 (4*CH3), 55.1 (OCH3), 83.2 (2*C(CH3)2) 105.5 (ArCH), 113.7 (ArC), 120.6 (ArCH), 125.8 (ArCH), 135.0 (ArC), 149.7 (ArC).
30% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 48 h; Inert atmosphere 2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (60a) (0303) 5-Bromo-2-methoxyaniline (500 mg, 2.48 mmol, 1.0 equiv), bis(pinacolato)diboron (691 mg, 2.72 mmol, 1.1 equiv), potassium acetate (730 mg, 7.44 mmol, 3.0 equiv) and Pd(dppf)Cl2 (54.4 mg, 74.4 μmol, 0.03 equiv) were dissolved under Argon atmosphere in 7 ml DMSO and the mixture was stirred at 80° C. for 48 h. Water was added and the aqueous layer was extracted with ethyl acetate three times. The combined organic layers were dried over magnesium sulfate, filtered and concentrated to dryness. The raw product was purified by flash chromatography; yield: 30percent (184 mg). 1H NMR (300 MHz, acetone-d6): δ 7.11-7.02 (m, 2H), 6.81 (d, J=7.9 Hz, 1H), 3.84 (s, 3H), 1.29 (s, 12H).
Reference: [1] Patent: US2015/18566, 2015, A1, . Location in patent: Paragraph 0685; 0686; 0687; 0688; 0689
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3767 - 3793
[3] Patent: US2016/318895, 2016, A1, . Location in patent: Paragraph 0303
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