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Product Details of [ 68819-84-1 ]

CAS No. :68819-84-1 MDL No. :MFCD08703140
Formula : C12H16BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DJNCXSGGAMADNN-UHFFFAOYSA-N
M.W : 286.17 Pubchem ID :12453839
Synonyms :

Calculated chemistry of [ 68819-84-1 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.42
Num. rotatable bonds : 5
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 67.66
TPSA : 38.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.91
Log Po/w (XLOGP3) : 3.11
Log Po/w (WLOGP) : 3.32
Log Po/w (MLOGP) : 3.06
Log Po/w (SILICOS-IT) : 2.73
Consensus Log Po/w : 3.03

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.52
Solubility : 0.0862 mg/ml ; 0.000301 mol/l
Class : Soluble
Log S (Ali) : -3.58
Solubility : 0.0747 mg/ml ; 0.000261 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.6
Solubility : 0.00719 mg/ml ; 0.0000251 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.84

Safety of [ 68819-84-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 68819-84-1 ]

* 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.

  • Upstream synthesis route of [ 68819-84-1 ]
  • Downstream synthetic route of [ 68819-84-1 ]

[ 68819-84-1 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 24424-99-5 ]
  • [ 26177-44-6 ]
  • [ 68819-84-1 ]
YieldReaction ConditionsOperation in experiment
99% With triethylamine In chloroform at 20℃; for 2 h; Step a (4-Bromobenzyl)-carbamic acid tert-butyl ester. To a stirred suspension of 4-bromo-benzylamine hydrochloride (968mg, 4.35mmol) and triethylamine (0.666ml, 4.79mmol) in chloroform (15ml) was added di-tert-butyldicarbonate (949mg, 4.35mmol). The resulting solution was stirred at ambient temperature for 2h and then diluted with DCM (40ml). The organic solution was washed sequentially with 10percent aqueous citric acid (40ml) and brine (40ml). The organic phase was dried over anhydrous magnesium sulfate and the filtrate evaporated at reduced pressure to afford the title compound (1.23g, 99percent). 1H NMR 7.48-7.43 (2H, m), 7.18 (2H, d, 8.4), 4.84 (1H, br s), 4.27 (2H, d, 5.7), 1.46 (9H, s).
99% With triethylamine In dichloromethane at 20℃; for 16 h; Preparation 36; (Z)-4-(2-Cyclohexylvinyl)-benzylamine; N-(fert-Butoxycarbonyl)-4-bromo-benzylamine; Slurry 4-bromo-benzylamine hydrochloride (25 g, 112.6 mmol) in DCM (400 mL). Add triethylamine (31.4 mL, 225.2 mmol) and di-tert-butyl-dicarbonate (24.55 g, 112.6 mmol) and stir the solution at room temperature for 16 h under a nitrogen atmosphere. Wash the mixture with water, dry the organic phase over Na2SO4 and concentrate in vacuo to obtain a solid. Wash the solid with hexane, filter and dry to obtain the desired intermediate as a white solid (31.735 g, 99percent) suitable for use without further purification. MS (ES+) m/z: 230 [M-(t-Bu)+H]+.
95% With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 16 h; 4-bromobenzylamine hydrochloride salt (3 g, 13.5 mmol, 1 eq) was dissolved in tetrahydrofuran (50 ml) was added sodium bicarbonate (2.27 g, 27 mmol, 2 eq) and dicarbonate di-tert-butyl ester (3.24 g, 14.9 mmol mol, 1.1 eq.), the reaction mixture was stirred for 16 hours at room temperature. Extracted with dichloromethane, the organic phase with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum to give 4-bromobenzylcarbamic acid tert-butyl ester (3.68 g, yield: 95percent).
1.6 g With sodium hydrogencarbonate In 1,4-dioxane at 20℃; for 3 h; To a solution of 1-(azidomethyl)-4-bromobenzene 2 (1.88 g, 8.95 mmol) in MeOH (10 mL) at room temperature, was addedPh3P (3.52 g, 13.4 mmol). The solution was heated to reflux and stirred for 1 h at this temperature. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in CH2C12, and 4 M HC1 (2.5 mL) in dioxane was added. The resulting precipitate was filtered and washed with hexanes to give crude amine compound as the HC1 salt. This amine was used for the next step without furtherpurification. The crude amine hydrochloride salt was suspended in dioxane (5 mL) and saturated aqueous NaHCO3 solution (10 mL) at room temperature. After addition of Boc2O (3.90 g, 17.9 mmol), the reaction mixture was stirred for 3 h at room temperature. The reaction mixture was diluted with EtOAc, and washed with H20 and brine. The organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure, and theresidue was purified by silica gel column chromatography using EtOAc/hexanes (10percent) to give 1.60 g (62percent) of 3 as a white solid. ‘H NMR spectra was consistent with literature data. Howell, S. J.; Spencer, N.; Philip D. Tetrahedron 2001, 57, 4945.

Reference: [1] Patent: EP1056733, 2004, B1, . Location in patent: Page 26
[2] Patent: WO2007/28083, 2007, A2, . Location in patent: Page/Page column 84
[3] Patent: CN105622638, 2016, A, . Location in patent: Paragraph 0312
[4] Tetrahedron, 2001, vol. 57, # 23, p. 4945 - 4954
[5] Chemistry - A European Journal, 2017, vol. 23, # 12, p. 2877 - 2883
[6] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 11, p. 2599 - 2606
[7] Patent: WO2012/31197, 2012, A1, . Location in patent: Page/Page column 410-411
[8] Patent: US2011/98311, 2011, A1,
[9] Patent: WO2013/90696, 2013, A1, . Location in patent: Page/Page column 84
[10] Patent: US2015/231142, 2015, A1, . Location in patent: Paragraph 1375
  • 2
  • [ 24424-99-5 ]
  • [ 3959-07-7 ]
  • [ 68819-84-1 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In dichloromethane at 0 - 20℃; (c) A solution of Boc2O (1.29g, 5.91mmol) in CH2Cl2 (10ml) was added to a suspension of 4-bromobenzylamine (1.00g, 5.38mmol) and Et3N (0.60g, 5.91mmol) in CH2Cl2 (10ml) for 5min at 0°C with a CaCl2 tube. The reaction mixture was stirred overnight at room temperature. Then, H2O (50ml) was added to the mixture, and the organic layer was separated. The aqueous layer was extracted with CHCl3 (50ml×3). The combined organic layer was washed with H2O (50ml×1) and then brine (50ml×1), dried over Na2SO4 (anhyd), filtered, and concentrated under reduced pressure to afford (4-bromobenzyl)carbamic acid tert-butyl ester (1.63g, quant. y.) as a colorless solid. Colorless powder (n-hexane). Mp 73–74°C. 1H NMR (300MHz/CDCl3) δ 1.46 (9H, s, t-Bu), 4.26 (2H, d, J=6.0Hz, CH2), 4.84 (1H, br s, NH), 7.16 (2H, d, J=8.4Hz, ArH), 7.45 (2H, d, J=8.4Hz, ArH).
96% With sodium hydroxide In 1,4-dioxane; water at 20℃; for 12 h; / Bromobenzylamine (0.93 g, 5 mmol) was dissolved in 1,4-dioxane (20 mL) and was treated with 10percent aq. NaOH (5 mL). To the stirred solution was added (Boc)20 (1.1 g, 5 mmol) dissolved in dioxane (10 mL). The mixture was stirred at room temperature for 12 hours. Water was added (20 mL) and the reaction mixture was extracted with ethyl acetate (3 x 50 mL). The organic phase was collected, washed with brine, dried over MgS04, filtered, and the solvent was evaporated to give the product as a white solid (1.37 g, 96percent).1H NMR (400 MHz, CDC13) δ (ppm) 7.44 (d, J= 8.1 Hz, 2H), 7.15 (d, J= 8.0 Hz, 2H), 4.86 (br s, 1H), 4.26 (d, J= 6.1 Hz, 2H), 1.45 (s, 9H). ESI-MS (m/z): 287 [M+2]+.
95% at 20℃; for 1 h; A solution of 4-bromobenzylamine (40.0g, 217.0 mmol) in THF (150 mL) was treated with di-tert-butyl dicarbonate (46.0g, 217 mmol) and stirred at rt for 1 h. The reaction mixture was concentrated in vacuo to afford a solid which was purified bychromatography (80:20 Hexanes: EtOAc) afforded the Boc protected amine (63.0 g, 95percent) as a white solid. A solution of the aryl bromide (30.0g, 98.0 mmol) in DMSO (100 mL) was treated with bis(pinacolato)diboron (30.0g, 118 mmol), KOAc (30.0g, 306 mmol), and PdCl2(dppf) (0.2 mmol) and warmed to 85 °C for 12 h. The reaction mixture was diluted with EtOAc (250 mL) and washed with water (2 x 150 mL) and brine (100 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo to afford a solid which was purification by chromatography (80:20 hexanes: EtOAc) afforded the desired cmpd (31.0 g, yield 97percent) as a white solid. ESI-MS (M+H)+: 334.
90% at 20℃; Cooling with ice Dissolve 10 mL of p-bromobenzylamine (1.0 g, 5.37 mmol) in a 100 mL round bottom flaskIn dichloromethane (DCM),Further, di-tert-butyl dicarbonate ((Boc) 2O (1.29 g, 5.91 mmol)) was gradually added dropwise.The DCM solution was stirred for 5 minutes under ice salt bath conditions and stirred at room temperature overnight.After the reaction was completed, the solvent was evaporated under reduced pressure, and water (40 mL) was added.The organic layer was combined and dried over anhydrous sodium sulfate.Evaporate the solvent and purify it by silica gel column chromatography. Eluent: petroleumEther (PE) / ethyl acetate (EA) = (20:1),A white solid (1.30 g, 90percent) was obtained.
89% With sodium carbonate In tetrahydrofuran; water for 12 h; Reflux General procedure: p-bromobenzamine (1 g, 5.37 mmol) was dissolved in THF:Water 2:5. Boc2O (1.41 g, 6.45 mmol) and Na2CO3 ( 1.67 g, 12.09 mmol) were then added and the mixture was refluxed for 12 h. Extraction was performed with 3x50 mL of EtOAc. The organic phase was dried with Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography using heptane : EtOAc 10:1. Yield: 1.36 g (89percent, 4.79 mmol). 1H-NMR (CDCl3, 400MHz) δ: 7.74 (dt, 2H), 7.18 (d, 2H), 4.28 (d, 2H), 1.48 (s, 9H). 13C-NMR (CDCl3, 400MHz) δ: 156, 138, 132, 129, 121, 80, 44, 28. GC-MS: 285 m/z. Analytical data can be found in literature.2 Tert-butyl-4-bromobenzylcarbamate (400 mg, 1.40 mmol) was dissolved in 10 mL of dry dioxane, potassium acetate (165 mg, 1.68 mmol), bis(pinacolato)diboron (426 mg, 1.68 mmol) and Pd(dppf)Cl2 (10 mg, 0.01 mmol) were added and the reaction was stirred at 100 ºC for 12 h. The mixture was stirred with 10 mL of sat. NaCl aqueous solution for 10 min. and extracted with 3x50 mL EtOAc. The combined organic phases were dried with Na2SO4 and concentrated in vacuo. The resulting residue was purified by flash chromatography using heptane : EtOAc 10:1. The pure compound was treated with 2.0 M HCl in diethyl ether and the resulting deprotected HCl salt was filtered off. Yield: 276 mg (73percent, 1.039 mmol). 1H-NMR (CDCl3 400MHz) δ: 7.69 (d, 2H), 7.48 (d, 2H), 4.03 (s, 2H), 1.29 (s, 12H). Analytical data can be found in literature.3
89% With triethylamine In dichloromethane at 0 - 20℃; for 1 h; General procedure: To a solution of (6chioropyridin3yl)methanamine (3.30 g, 23.1 mmol) inDCM (30 inL) was added TEA (4.84 mL. 34.7 rnmoi) and BOC2O (6.72 mL, 28.9 mrnol), at 0 °C. The resulting mixture was stirred at ambient temperature for iii. The reaction was quenched with saturated sodium bicarbonate solution (50 mL) and extracted with DCM (3x l0() rnL). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain Intermediate 2A (5.50 g, 98.0percent) as a yellow oil. ‘H NMR (300 MHz, DMSO-.ck) ö ppm1.38 (s, 9 H), 4,14 (d, J= 6.04 Hz, 2 H), 7.48 (d, J= 7.93 Hz, 2 H), 771 (dd, J= 8.12,2.46 Hz, I H), 8.28 (d, J = 189 Hz, I H). LCMS ,MethodD): retention time 2.31 mm,jM-H1-{i 243. 1.
78% With triethylamine In dichloromethane at 0 - 20℃; General procedure: The hydrogenation of 3-phenylpropylazide (Table 2, entry 1) is given as an example. 3-Phenylpropylazide (3a) (207.2 mg, 1.29 mmol) was charged into an Ar-filled 100 mL glass autoclave equipped with a Teflon-coated magnetic stirring bar. THF (1.2 mL) degassed by three freeze–thaw cycles was introduced via a Teflon cannula, followed by the addition of a solution of the Pd NPs catalyst in DMF (5.0 mM, 20 μL, 0.10 μmol, S/Pd = 12,900:1). Hydrogen was introduced into the reaction vessel until the pressure gauge indicated 8 atm, and then the pressure was carefully released to 1 atm by opening the stop valve. This procedure was repeated five times,and finally hydrogen was pressurized to 8 atm. The vessel was placed in a water bath controlled at 50 °C, and the reaction mixture was vigorously stirred for 16 h. After careful venting of the hydrogen, the reaction mixture was concentrated under reduced pressure. 1,1,2,2-Tetrachloroethane (124.0 mg, 0.739 mmol) was added as an internal standard for the NMR analysis, and the produced 3-phenylpropylamine (4a) was quantified (99.5percent). The reaction mixture was carefully concentrated under reduced pressure to remove THF. To this crude mixture were added dichloromethane (5 mL) and triethylamine (0.45 mL, 3.2 mmol), and the mixture was cooled to 0 °C. Boc2O (726.7 mg, 3.3 mmol) was added at 0 °C, and the solution was stirred at room temperature over night. The reaction mixture was diluted by addition of dichloromethane (10 mL). The solution was washed 3 times successively with water, then once with brine, and dried over magnesium sulfate. After removal of the drying agent by filtration, the solution was concentrated under reduced pressure. The residual oil was purified by silica gel column chromatography (hexane : ethyl acetate = 20:1), giving pure carbamate Boc-4a as a colorless oil (248.3 mg, 87percent).

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 20, p. 3557 - 3560
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 14, p. 3720 - 3731
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 33, p. 8666 - 8670[4] Angew. Chem., 2013, vol. 125, # 33, p. 8828 - 8832,5
[5] Patent: WO2014/85453, 2014, A2, . Location in patent: Page/Page column 58-59
[6] Patent: WO2015/89327, 2015, A1, . Location in patent: Paragraph 0336
[7] Patent: CN108794490, 2018, A, . Location in patent: Paragraph 0056; 0057; 0058
[8] Tetrahedron Letters, 2013, vol. 54, # 3, p. 213 - 216
[9] Patent: WO2018/93569, 2018, A1, . Location in patent: Page/Page column 45; 46; 55
[10] Tetrahedron Letters, 2016, vol. 57, # 37, p. 4183 - 4186
[11] Patent: US2003/199689, 2003, A1, . Location in patent: Page/Page column 48
[12] MedChemComm, 2013, vol. 4, # 12, p. 1562 - 1570
[13] Patent: WO2014/146490, 2014, A1, . Location in patent: Page/Page column 75
[14] Patent: WO2014/146246, 2014, A1, . Location in patent: Page/Page column 63
  • 3
  • [ 24424-99-5 ]
  • [ 68819-84-1 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydrogencarbonate In methanol for 4 h; N-[4-(5-Cyano-2-methoxy-pyridin-3-yl)-benzyl]-2-trifluoromethoxy-benzenesulfonamide To a solution of 4-aminomethylphenylboronic acid hydrochloride (2.0 g, 13.2 mmol) in methanol (20 ml) was added di-tert-butyl dicarbonate (3.16 g, 15.5 mmol) and sodium bicarbonate (3.32 g, 19.8 mmol). The mixture was sonicated for 4 h then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over anhydrous magnesium sulfate and the solvent evaporated to give (4-bromo-benzyl)-carbamic acid tert-butyl ester (1.8 g, 13.2 mmol, 100percent) as a white solid. To 6-chloro-nicotinonitrile (15 g, 0.11 mol) under argon atmosphere was added 25percent sodium methoxide in methanol (11.7 g, 0.22 mol) and the mixture heated under reflux for 20 h. The methanol was evaporated and the residue partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were washed with water, brine, dried over anhydrous magnesium sulfate and the solvent evaporated to give 6-methoxy-nicotinonitrile (17.0 g, 0.13 mol, 117percent) as a white solid. To 6-methoxy-nicotinonitrile (13.2 g, 99 mmol) in acetic acid (32 ml) was added sodium acetate (8.1 g, 99 mmol). The mixture was stirred and a solution of bromine (31.5 g, 197 mmol) in acetic acid (32 ml) added. The mixture was heated to 80° C. for 48 h. The reaction mixture was poured into water and extracted with diethyl ether. The organic phase was washed with 4M aqueous sodium hydroxide solution, 5percent sodium thiosulfate solution, dried over anhydrous potassium carbonate and the solvent was evaporated to give 5-bromo-6-methoxy-nicotinonitrile (11.9 g, 56 mmol, 57percent). To a solution of 2-methoxy-5-cyanopyridine-3-boronic acid (1.0 g, 4.0 mmol) in 1,2-dimethoxyethane (10 ml) was added (4-bromo-benzyl)-carbamic acid tert-butyl ester (0.42 g, 2.0 mmol), tetrakis(triphenylphosphine)palladium (0) (114 mg, 0.1 mmol) and 2M aqueous sodium carbonate (1 ml, 2.0 mmol). The reaction was heated to 150° C. for 10 min in a microwave over. The mixture was concentrated under reduced pressure and partitioned between ethyl acetate and water. The organic phase was washed with water, then brine, dried over anhydrous magnesium sulfate and the solvent evaporated. The residue was purified on silica gel eluting with 5:1 heptane/ethyl acetate to give [4-(5-cyano-2-methoxy-pyridin-3-yl)-benzyl]-carbamic acid tert-butyl ester as a white solid (0.5 g, 1.47 mmol, 37percent). To a solution of [4-(5-cyano-2-methoxy-pyridin-3-yl)-benzyl]-carbamic acid tert-butyl ester (0.5 g, 1.5 mmol) in dichloromethane (5 ml) at 0° C. was added trifluoroacetic acid (5 ml, 28 mmol). The reaction mixture was stirred for 30 min at 0° C. before the solvent was evaporated and the residue purified on a SCX column (eluted with 2M ammonia in methanol) to give 5-(4-aminomethyl-phenyl)-6-methoxy-nicotinonitrile as a clear glass (0.39 g, 1.6 mmol, 107percent). To a solution of 5-(4-aminomethyl-phenyl)-6-methoxy-nicotinonitrile (57.3 mg, 0.24 mmol) in dichloromethane (2 ml) was added triethylamine (73.0 mg, 0.72 mmol) and 2-(trifluoromethoxy)benzenesulfonyl chloride. The reaction mixture was agitated for 20 hours and the solvent evaporated under reduced pressure. The crude product was taken up in dimethyl sulfoxide (1 ml) and purified by preparatory LCMS. The solvent was evaporated under reduced pressure to give the title compound (19.1 mg, 0.04 mmol, 17percent). 1H NMR (400 MHz, DMSO-d6): δ 8.68 (d, 1H), 8.47 (t, 1H), 8.15 (d, 1H), 7.90 (m, 1H), 7.73 (m, 1H), 7.45-7.55 (m, 4H), 7.31 (d, 2H), 4.19 (d, 2H), 3.96 (s, 3H) ppm; MS (ESI) m/z: 464.3 [M+H]+.
Reference: [1] Patent: US2007/149577, 2007, A1, . Location in patent: Page/Page column 17-18
  • 4
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  • [ 68819-84-1 ]
Reference: [1] Chemistry - A European Journal, 2010, vol. 16, # 15, p. 4557 - 4566
  • 5
  • [ 589-15-1 ]
  • [ 68819-84-1 ]
Reference: [1] Patent: WO2013/90696, 2013, A1,
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 14, p. 3720 - 3731
  • 6
  • [ 107047-10-9 ]
  • [ 68819-84-1 ]
Reference: [1] Patent: WO2013/90696, 2013, A1,
[2] Tetrahedron Letters, 2016, vol. 57, # 37, p. 4183 - 4186
  • 7
  • [ 153171-22-3 ]
  • [ 68819-84-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 14, p. 3720 - 3731
  • 8
  • [ 66389-77-3 ]
  • [ 589-15-1 ]
  • [ 68819-84-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1978, p. 1088 - 1090
  • 9
  • [ 68819-84-1 ]
  • [ 73183-34-3 ]
  • [ 330794-35-9 ]
YieldReaction ConditionsOperation in experiment
97% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 85℃; for 12 h; A solution of 4-bromobenzylamine (40.0g, 217.0 mmol) in THF (150 mL) was treated with di-tert-butyl dicarbonate (46.0g, 217 mmol) and stirred at rt for 1 h. The reaction mixture was concentrated in vacuo to afford a solid which was purified bychromatography (80:20 Hexanes: EtOAc) afforded the Boc protected amine (63.0 g, 95percent) as a white solid. A solution of the aryl bromide (30.0g, 98.0 mmol) in DMSO (100 mL) was treated with bis(pinacolato)diboron (30.0g, 118 mmol), KOAc (30.0g, 306 mmol), and PdCl2(dppf) (0.2 mmol) and warmed to 85 °C for 12 h. The reaction mixture was diluted with EtOAc (250 mL) and washed with water (2 x 150 mL) and brine (100 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo to afford a solid which was purification by chromatography (80:20 hexanes: EtOAc) afforded the desired cmpd (31.0 g, yield 97percent) as a white solid. ESI-MS (M+H)+: 334.
Reference: [1] Patent: WO2015/89327, 2015, A1, . Location in patent: Paragraph 0336
[2] Chemical Communications, 2013, vol. 49, # 30, p. 3110 - 3112
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 33, p. 8666 - 8670[4] Angew. Chem., 2013, vol. 125, # 33, p. 8828 - 8832,5
[5] Patent: US2007/179115, 2007, A1, . Location in patent: Page/Page column 19
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