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[ CAS No. 73183-34-3 ]

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2D
Chemical Structure| 73183-34-3
Chemical Structure| 73183-34-3
Structure of 73183-34-3 *Storage: {[proInfo.prStorage]}

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Product Details of [ 73183-34-3 ]

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

Computed Properties of [ 73183-34-3 ]

TPSA : 36.9 H-Bond Acceptor Count : 4
XLogP3 : - H-Bond Donor Count : 0
SP3 : 1.00 Rotatable Bond Count : 1

Safety of [ 73183-34-3 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

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   1~16

  • 1
  • [ 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
  • 2
  • [ 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
  • 3
  • [ 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
  • 4
  • [ 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
  • 5
  • [ 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
  • 6
  • [ 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
  • 7
  • [ 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
  • 8
  • [ 694-85-9 ]
  • [ 73183-34-3 ]
  • [ 1002309-52-5 ]
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 21, p. 4745 - 4752
  • 9
  • [ 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
  • 10
  • [ 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
  • 11
  • [ 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
  • 12
  • [ 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
  • 13
  • [ 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
  • 14
  • [ 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
  • 15
  • [ 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
  • 16
  • [ 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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Chemical Structure| 99810-76-1

[ 99810-76-1 ]

2-(tert-Butyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.52

Chemical Structure| 126689-01-8

[ 126689-01-8 ]

2-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.50