* 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.
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; Darkness
A 1 M solution of compound 8a in DMF was cooled to 0 °C in the absence of light and NBS (1.0 eq.) was added. The mixture was allowed to warm to room temperature, stirred overnight and then diluted with DCM . The solution was extracted with H20 and brine. The combined aqueous layers were extracted with DCM. The combined organic layers were dried over MgSC and the solvent was removed in vacuo. The resulting light yellow oil was purified via column chromatography (silica gel, petroleum ether) yielding compound 7a as a colorless oil (99percent). H NMR (300.13 MHz, CDCI3) δ (ppm) = 7.18 (d, 3J = 5.5 Hz, 1 H, H9), 6.79 (d, 3J = 5.5 Hz, 1 H, H8), 2.56 (t, 3J = 7.7 Hz, 2 H, H6), 1.63-1.51 (m, 2 H , H5), 1.40-1.24 (m, 6 H, H4-2), 0.89 (t, 3J = 6.8 Hz, 3 H, H1).
86%
With N-Bromosuccinimide In tetrahydrofuran at 0℃; for 2 h;
First, 2-bromo-3-hexylthiophene was synthesized via the reaction of 3-hexylthiophene with N-bromosuccinimide (NBS). To a flask equipped with magnetic stirrer, 3-hexylthiophene (10.000 g, 59.4 mmol) and THF (100 mL) were charged with vigorous stirring and then NBS (10.580 g, 59.4 mmol) was added at 0 °C. The reaction was carried out at 0 °C for 2 h and then 100 mL of deionized water was added. The organic layer was extracted out with diethyl ether and the organic layer was successively washed with 10percent aqueous solutions of Na2S2O3, KOH and deionized water and dried over anhydrous magnesium sulfate (MgSO4). The filtrate was distillated under reduced pressure and the colorless oil liquid (12.730 g) wasobtained with the yield of 86percent. 1H NMR (ppm, CDCl3): 7.18 (d, 1H,-CHCHS-), 6.79 (d, 1H,-CCHCH-), 2.56 (t, 2H,-CCH2CH2-), 1.57 [quint, 2H,-CH2CH2(CH2)3-],1.31 [m, 6H, -CH2(CH2)3CH3] and 0.89 [t, 3H,-(CH2)3CH3].
77%
With N-Bromosuccinimide In acetic acid at 22℃; for 2.5 h;
2-Bromo-3-hexylthiophene was prepared similarly to a method described by Carlsen et al.10 and was modified as follows: 3-hexylthiophene (12.0 g, 71.3 mmol) was dissolved in glacial acetic acid (100 mL) under an air atmosphere. Then NBS (12.7 g, 71.5 mmol) was added in one portion. The reaction mixture was stirred for 2.5 h at 22 °C. Then the solution was poured into water (200 mL) and diethyl ether (250 mL). After extraction, the organic phase was separated and washed with aqueous NaOH (2 M, 5 x 150 mL), followed by water (3 x 150 mL). The organic layer was dried over MgSO4 and then the solvent was removed in vacuo. The crude product was purified by vigreux distillation (130 °C, 4 x 10-2 mbar) to receive 13.5 g (77percent, lit.10 92percent) of light yellow oil.
Reference：
[1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 11, p. 1752 - 1763
[2] Patent: WO2015/15397, 2015, A1, . Location in patent: Page/Page column 50
[3] Chemistry - A European Journal, 2014, vol. 20, # 49, p. 16128 - 16137
[4] Journal of Materials Chemistry, 2011, vol. 21, # 5, p. 1462 - 1469
[5] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 9, p. 1933 - 1941
[6] Chemistry Letters, 2003, vol. 32, # 3, p. 264 - 265
[7] Journal of Materials Chemistry A, 2016, vol. 4, # 7, p. 2509 - 2516
[8] Journal of the American Chemical Society, 2006, vol. 128, # 43, p. 13988 - 13989
[9] Journal of the American Chemical Society, 2008, vol. 130, # 48, p. 16324 - 16329
[10] Macromolecules, 2004, vol. 37, # 4, p. 1169 - 1171
[11] Journal of the American Chemical Society, 2006, vol. 128, # 33, p. 10930 - 10933
[12] Macromolecules, 2014, vol. 47, # 3, p. 1008 - 1020
[13] Chemistry - An Asian Journal, 2016, vol. 11, # 24, p. 3557 - 3567
[14] Journal of Materials Chemistry A, 2017, vol. 5, # 17, p. 7811 - 7815
[15] Macromolecules, 2013, vol. 46, # 11, p. 4548 - 4557
[16] Journal of the American Chemical Society, 2013, vol. 135, # 37, p. 13695 - 13698
[17] Journal of Polymer Science, Part A: Polymer Chemistry, 2014, vol. 52, # 8, p. 1055 - 1058
[18] Journal of Nanoscience and Nanotechnology, 2011, vol. 11, # 5, p. 4367 - 4372
[19] Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 8, p. 2363 - 2378
[20] Journal of Materials Chemistry, 2008, vol. 18, # 16, p. 1895 - 1902
[21] Polymer, 2015, vol. 69, p. 193 - 203
[22] Tetrahedron, 2009, vol. 65, # 52, p. 10797 - 10815
[23] Journal of the American Chemical Society, 1995, vol. 117, # 1, p. 233 - 244
[24] Journal of Materials Chemistry, 1999, vol. 9, # 9, p. 2109 - 2115
[25] Organic Letters, 2013, vol. 15, # 18, p. 4666 - 4669
[26] Tetrahedron, 2015, vol. 71, # 33, p. 5399 - 5406
[27] Journal of the American Chemical Society, 2009, vol. 131, # 45, p. 16573 - 16579
[28] Macromolecules, 2004, vol. 37, # 24, p. 8951 - 8958
[29] Journal of the Chemical Society. Perkin Transactions 2, 1997, # 8, p. 1597 - 1604
[30] Journal of Organic Chemistry, 1993, vol. 58, # 4, p. 904 - 912
[31] Molecular Crystals and Liquid Crystals, 2011, vol. 538, p. 223 - 231
[32] Journal of the American Chemical Society, 1997, vol. 119, # 45, p. 11106 - 11107
[33] Molecular Crystals and Liquid Crystals, 2007, vol. 470, # 1, p. 353 - 358
[34] New Journal of Chemistry, 2001, vol. 25, # 2, p. 318 - 321
[35] Angewandte Chemie - International Edition, 2009, vol. 48, # 43, p. 8014 - 8017
[36] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 1, p. 193 - 195
[37] Patent: EP2266982, 2010, A1, . Location in patent: Page/Page column 36-38
[38] Journal of the American Chemical Society, 2011, vol. 133, # 22, p. 8654 - 8661
[39] Macromolecules, 2012, vol. 45, # 16, p. 6424 - 6437
[40] Chemical Science, 2013, vol. 4, # 8, p. 3317 - 3331
[41] Journal of the American Chemical Society, 2013, vol. 135, # 32, p. 11724 - 11727
[42] Chemical Communications, 2013, vol. 49, # 80, p. 9146 - 9148
[43] Journal of Polymer Science, Part A: Polymer Chemistry, 2014, vol. 52, # 1, p. 76 - 86
[44] Chemistry - An Asian Journal, 2014, vol. 9, # 12, p. 3549 - 3557
[45] Macromolecules, 2015, vol. 48, # 10, p. 3269 - 3281
[46] Journal of Nanoscience and Nanotechnology, 2016, vol. 16, # 6, p. 5639 - 5645
[47] Patent: KR2018/27475, 2018, A, . Location in patent: Paragraph 0178; 0184-0189
2
[ 116971-11-0 ]
[ 69249-61-2 ]
Reference：
[1] New Journal of Chemistry, 2001, vol. 25, # 2, p. 318 - 321
3
[ 68-12-2 ]
[ 116971-11-0 ]
[ 291535-21-2 ]
[ 69249-61-2 ]
Reference：
[1] Bulletin of the Chemical Society of Japan, 2007, vol. 80, # 2, p. 371 - 386
Reference：
[1] Journal of the American Chemical Society, 2014, vol. 136, # 43, p. 15130 - 15133
9
[ 69249-61-2 ]
[ 1693-86-3 ]
[ 125607-30-9 ]
[ 135926-93-1 ]
Reference：
[1] Bulletin of the Chemical Society of Japan, 1998, vol. 71, # 2, p. 483 - 495
[2] Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 8, p. 2363 - 2378
[3] Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 8, p. 2363 - 2378
10
[ 69249-61-2 ]
[ 1693-86-3 ]
[ 125607-30-9 ]
[ 135926-93-1 ]
Reference：
[1] Bulletin of the Chemical Society of Japan, 1998, vol. 71, # 9, p. 2229 - 2237
11
[ 69249-61-2 ]
[ 1693-86-3 ]
Reference：
[1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 11, p. 1752 - 1763
[2] Organic and Biomolecular Chemistry, 2007, vol. 5, # 11, p. 1752 - 1763
[3] Organic and Biomolecular Chemistry, 2007, vol. 5, # 11, p. 1752 - 1763
12
[ 69249-61-2 ]
[ 154717-20-1 ]
[ 1693-86-3 ]
[ 125607-30-9 ]
[ 170702-09-7 ]
Reference：
[1] Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 8, p. 2363 - 2378
13
[ 69249-61-2 ]
[ 116971-11-0 ]
Reference：
[1] Journal of the American Chemical Society, 2004, vol. 126, # 46, p. 15295 - 15308
[2] Bulletin of the Chemical Society of Japan, 1995, vol. 68, # 8, p. 2363 - 2378
With palladium(II) trifluoroacetate; silver(l) oxide In dimethyl sulfoxide at 80℃; for 10 h;
To a 25 mL reaction tube,3.4 mg (5 molpercent) of Pd (Tfa) 2,Ag2O (0.8 mmol),Compound 21 (0.2 mmol, 1 eq),After purging with nitrogen for 3 times, 1 mL of dimethylsulfoxide (DMSO)Compound 22 (0.80 mmol) was injected,After stirring at 80 ° C for 10 hours,Compound C-13,The yield is 64percent.
With trichlorophosphate In 1,2-dichloro-ethane at 90℃; for 24h; Inert atmosphere;
2.4.4 5-bromo-4-hexylthiophene-2-carbaldehyde (4)
In an ice bath, phosphorus oxychloride (15mL) and DMF (12mL) were added into a 250mL two-necked flask, and stirred under a nitrogen atmosphere. Then, a solution of 2-bromo-3-hexylthiophene (1.0g, 4.1mmol) in 40mL dichloroethane was added and stirred at 90°C for 24h under a nitrogen atmosphere. After cooling down to room temperature, the mixture was poured into ice water, the mixture was washed with water and dried on MgSO4. After filtration and concentration under reduced pressure, compound 4 was obtained as yellow oil using silica gel column chromatography with petroleum ether: ethyl acetate (20: 1, v: v) as the eluent (1.1g, 90%). 1H NMR (600MHz, CDCl3) δ=10.04 (s, 1H), 7.99 (d, J=8.0Hz, 2H), 7.63 (d, J=8.0Hz, 2H), 7.26 (s, 1H), 3.37 (s, 4H), 2.64-2.61 (m, 2H), 1.56-1.52 (m, 2H), 1.23-1.17 (m, 6H), 0.80 (t, J=6.9Hz, 3H). 13C NMR (151MHz, CDCl3) δ=182.20; 181.95; 141.40; 139.78; 137.00; 122.11; 31.52; 29.38; 28.80; 27.92; 22.55; 14.05. MALDI-TOF: m/z [M]+ cacld. C11H15BrOS, 274.0027; found: 274.0025.
87.3%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 1h; Inert atmosphere;
Stage #2: 3-hexyl-2-bromothiophene In 1,2-dichloro-ethane at 90℃; for 4h; Inert atmosphere;
4.1.6 2-Bromo-3-hexyl-5-formylthiophene (9)
To the cold solvent dry DMF (25 ml) at 0 °C, POCl3 (22.5 ml) was added dropwise. The solution was stirred for 1 h. Then 2-bromothiophene (8) (3.31 g, 13.4 mmol) dissolved in 1,2-dechloroethane (30 ml) was injected. The reaction was kept at 90 °C for 4 h under N2. After cooling to room temperature, the reaction mixture was poured to 200 ml ice water, neutralized with saturated NaOH solution, and then extracted with dichloromethane twice. The combined organic layer was washed with H2O and brine, dried over Na2SO4, and evaporated under reduced pressure. The crude was purified by column chromatography (petroleum/EtOAc=5/1) to obtain compound 9 (3.217 g, 87.3%) as yellow liquid. MS(EI): m/z=274 (M+). 1H NMR (400 MHz, CDCl3) δ: 9.75 (s, 1H), 7.16 (s, 1H), 2.60 (t, 2H), 1.62-1.57 (m, 2H), 1.36 (m, 6H), 0.88 (t, 3H).
85%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 1h; Inert atmosphere;
Stage #2: 3-hexyl-2-bromothiophene at 90℃; for 10h; Inert atmosphere;
83%
Stage #1: 3-hexyl-2-bromothiophene With lithium diisopropyl amide In tetrahydrofuran at -78℃;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - 20℃;
83%
With trichlorophosphate In dichloromethane at 90℃; for 24h; Inert atmosphere;
Synthesis of 5-bromo-3-hexylthiophene-2-carbaldehyde (1)
A mixture of POCl3 and DMF as vilsmeier reagent (11.32 g, 50.00 mmol) was added into a2-bromo-3-hexylthiophene (2.472 g, 10.00 mmol) in dichloroethane. Themixture was stirredfor 24 hours at 90°C under N2 atmosphere. A portion of 100 mL of water was added to themixture and allowed to cool to roomtemperature. The mixture was extracted withmethylenechloride (MC) and the extracted organic layer was dried over anhydrous MgSO4. The organicsolvent was removed by using a rotary evaporator. The crude product was purified by columnchromatography on silica gel using MC/n-hexane. The yield of clear yellow liquid was2.284 g (83.00%). 1H-NMR (400 MHz, CDCl3, ppm): δ 9.75 (s, 1H), 7.5 (s, 1H), 2.62∼2.59(t, J = 7.6 Hz, 2H), 1.63∼1.58 (m, 2H), 1.37∼1.31 (m, 6H), 0.91∼0.88 (t, J = 6.8 Hz, 6H).13C NMR (100 MHz, CDCl3, ppm) δ.182.43, 146.57, 143.02, 139.37, 120.28, 31.86, 31.23,28.91, 27.13, 22.65, 14.12.13C NMR (100MHz, CDCl3, ppm) δ.182.06, 143.91, 141.31, 139,74,122.05, 31.47, 29.39, 28.73, 27.88, 22.49, 14.01. Anal. Calcd. for C11H15BrOS: C, 48.01; H,5.49; Br, 29.03; O, 5.81; S, 11.65. Found: C, 47.97; H, 5.34; Br, 29.01; O, 5.66; S, 11.57.
70%
Stage #1: 3-hexyl-2-bromothiophene With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at 20℃; for 12h; Inert atmosphere;
70%
With Vilsmeier reagent; trichlorophosphate In 1,2-dichloro-ethane at 90℃; for 24h; Inert atmosphere;
1.1 (1) Synthesis of 5-Bromo-4-hexylthiophene-2-carbaldehyde (Compound 3)
POCl3 (767 mg, 5 mmol) as vilsmeier reagentAnd a mixture of DMF (365 mg, 5 mmol) was added dropwise to a solution of 2-bromo-3-hexylthiophene (1.24 g, 5 mmol) in dichloroethane.The mixture was stirred under N2 atmosphere at 90° C. for 24 hours. After cooling to room temperature, water was added to the mixture and the mixture was extracted with dichloromethane (MC). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), and the solvent was removed using a rotary evaporator. The resulting liquid was purified by silica gel column chromatography using MC/n-hexane as eluent to obtain a pale yellow liquid (959 mg, 70%).
67%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 3-hexyl-2-bromothiophene In 1,2-dichloro-ethane at 90℃; for 12h;
67%
Stage #1: 3-hexyl-2-bromothiophene With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 1h; Schlenk technique; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78 - 20℃; for 12.5h; Schlenk technique; Inert atmosphere;
I-1 (Synthesis of 2-Bromo-5-formyl-3-hexylthiophene (A))
2-Bromo-3-hexylthiophene (8.3 g, 30 mmol) and dehydrated THF (100 mL) were placed in a Schlenk tube under a nitrogen atmosphere at -78 ° C. and stirred. Further, lithium diisopropylamide (LDA) (15 ml, 2.0 M hexane solvent, 30 mmol) was slowly added and stirred for 1 hour. N, N-dimethylformamide (DMF) (2.2 g, 30 mmol) was added and the mixture was stirred for 30 minutes and then stirred at room temperature for 12 hours. After diluted hydrochloric acid was added, it was extracted with chloroform, dried with sodium sulfate, and the solvent was removed with an evaporator. The residue was separated by column chromatography (silica gel, chloroform: hexane = 1: 1) to obtain an orange oil (5.5 g, yield 67%).
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trichlorophosphate at 80℃;
Stage #1: 3-hexyl-2-bromothiophene With trichlorophosphate at 0℃; for 1h; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In 1,2-dichloro-ethane at 90℃; for 4h; Inert atmosphere;
Stage #1: 3-hexyl-2-bromothiophene With magnesium In diethyl ether for 2h; Inert atmosphere; Reflux;
Stage #2: 2-bromo-5-hexylthiophene With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether at 0℃; for 12h; Inert atmosphere;
With α-picoline; silver(I) acetate; palladium diacetate In dimethyl sulfoxide at 100℃; for 9h; chemoselective reaction;
42%
With silver(I) acetate; palladium diacetate In dimethyl sulfoxide at 80℃; for 10h;
31 Example 31
To a 25 mL reaction tube,2.24 mg (5 mol%) of Pd (OAc) 2,AgOAc (0.8 mmol),Compound 33 (0.2 mmol, 1 eq),After three times of nitrogen replacement, 2 mL of dimethylsulfoxide (DMSO)Compound 22 (0.40 mmol) was injected,After stirring at 80 ° C for 10 hours,Compound C-28,The yield is 42%.
Stage #1: 3-hexyl-2-bromothiophene With magnesium In diethyl ether for 1h; Inert atmosphere; Reflux;
Stage #2: 2,6-dichloro-1,5-naphthyridine With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether at 20℃; Inert atmosphere; Reflux;
6 Preparation of compound 1d
A suspension of magnesium turnings (3.3 eq) in dry diethylether was stirred for 1 h under an argon atmosphere. Compound 7a (3 eq) was added. The Grignard reaction was initiated by careful heating of the solution accompanied by a change of color to brown and tarnishing. When the exothermic reaction was completed, the reaction mixture was heated to reflux for 1 h. After cooling to room temperature compound 3a (1 eq) and Ni(dppp)Cl2 (2 mol%) were added and the solution was heated to reflux overnight. The completion of the reaction was checked via TLC. Then the mixture was quenched with water. The organic phase was separated and the aqueous layer was extracted with DCM. The combined organic layers were dried over MgS04 and the solvent was removed under reduced pressure. Compound 1 d was purified via column chromatography, yielding yellow crystals. 1H NMR (300.13 M Hz, CDCI3) δ (ppm) = 8.34 (d, 3 J = 8.7 Hz, 2 H, H13), 7.89 (d, J = 8.7 Hz, 2 H, H12), 7.37 (d, 3J = 5.1 Hz, 2 H, H1 1 ), 7.04 (d, 3J = 5.1 Hz, 2 H, H9), 3.06 (t, 3J = 7.9 Hz, 4 H, H6), 1.80-1.65 (m, 4 H, H5), 1.47-1.23 (m, 12 H, H2-4), 0.87 (t, 3 J = 7.0 Hz, 6 H, /-/1 ).
1,1'-bis<(trimethylsiloxy)carbonyl>trimethylamine[ No CAS ]
[ 1416241-98-9 ]
Yield
Reaction Conditions
Operation in experiment
80%
Stage #1: 3-hexyl-2-bromothiophene; boron trichloride With 2,6-dichloropyridine; aluminum (III) chloride In dichloromethane at 0 - 23℃; for 1h; Inert atmosphere; Schlenk technique;
Stage #2: 1,1'-bis<(trimethylsiloxy)carbonyl>trimethylamine With Dimethyl-p-toluidine In dichloromethane; acetonitrile at 0 - 23℃; for 14h; Inert atmosphere; Schlenk technique;
2-chloro-3-methyl-5-(3-hexylthiophen-2-yl)thiophene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
79%
General procedure: To a 20 mL Schlenk tube equipped with a magnetic stirring bar were added 2-chloro-3-hexyl<strong>[14345-97-2]thiophene</strong> (1a; 65 muL, 0.30 mmol) and a solution of TMPMgCl·LiCl (1 M in THF, 0.36 mL, 0.36 mmol) at r.t. under a nitrogen atmosphere. After stirring at r.t. for 3 h, 2-bromo-3-hexyl-<strong>[14345-97-2]thiophene</strong> (2A; 72 muL, 0.36 mmol), Pd-PEPPSI-SIPr (4.1 mg, 6 mumol) and THF (3.0 mL) were added successively. The resulting solution was stirred and heated at 60 C for 24 h. After cooling the resulting mixture to r.t., the reaction was terminated by pouring the mixture into 1M HCl aq and chloroform to give two phases. The aqueous layer was extracted twice with chloroform and the combined organic extracts were dried over anhydrous sodium sulfate. After removal of the solvent, the residual crude oil was purified by column chromatography (hexanes) on silica gel to afford 3Aa. Yield: 79.7 mg (77%)
2-chloro-5-(3-hexylthiophen-2-yl)thiophene[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
82%
Stage #1: 2-thienyl chloride With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex In tetrahydrofuran at 25℃; for 3h; Inert atmosphere; Schlenk technique;
Stage #2: 3-hexyl-2-bromothiophene With Pd-PEPPSI-SIPr In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; Schlenk technique;
2-Chloro-3-hexyl-5-(3-hexylthiophen-2-yl)thiophene (3Aa)
General procedure: To a 20 mL Schlenk tube equipped with a magnetic stirring bar were added 2-chloro-3-hexylthiophene (1a; 65 μL, 0.30 mmol) and a solution of TMPMgCl·LiCl (1 M in THF, 0.36 mL, 0.36 mmol) at r.t. under a nitrogen atmosphere. After stirring at r.t. for 3 h, 2-bromo-3-hexyl-thiophene (2A; 72 μL, 0.36 mmol), Pd-PEPPSI-SIPr (4.1 mg, 6 μmol) and THF (3.0 mL) were added successively. The resulting solution was stirred and heated at 60 °C for 24 h. After cooling the resulting mixture to r.t., the reaction was terminated by pouring the mixture into 1M HCl aq and chloroform to give two phases. The aqueous layer was extracted twice with chloroform and the combined organic extracts were dried over anhydrous sodium sulfate. After removal of the solvent, the residual crude oil was purified by column chromatography (hexanes) on silica gel to afford 3Aa. Yield: 79.7 mg (77%)
With palladium(II) trifluoroacetate; silver(l) oxide; In dimethyl sulfoxide; at 80℃; for 10h;
To a 25 mL reaction tube,3.4 mg (5 mol%) of Pd (Tfa) 2,Ag2O (0.8 mmol),Compound 21 (0.2 mmol, 1 eq),After purging with nitrogen for 3 times, 1 mL of dimethylsulfoxide (DMSO)Compound 22 (0.80 mmol) was injected,After stirring at 80 C for 10 hours,Compound C-13,The yield is 64%.
With palladium(II) trifluoroacetate; silver(l) oxide; In dimethyl sulfoxide; at 80℃; for 10h;
To a 25 mL reaction tube,3.4 mg (2.5 mol%) of Pd (Tfa) 2,Ag2O (0.8 mmol),Compound 23 (1.2 mmol, 1 eq),After purging with nitrogen for 3 times, 1 mL of dimethylsulfoxide (DMSO)Compound 22 (0.4 mmol, 1 eq) was injected,After stirring at 80 C for 10 hours,Compound C-14 (ie compound 21),The yield is 71%.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
