* 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 tetrahydrofuran; methanol at 0℃; for 3.5 h;
Synthesis of methyl 5 -bromo- 1H-pyrrole-2-carboxylate (53): Methyl 1H-pyrrole-2-carboxylate (52; lOg, 80 mmol) was dissolved in 800 mL of THF and 400 mL of MeOH. The mixture was cooled to 0 °C. NBS (15 g, 8 4 mmol) was added in 5 portions in 1.5 h. After the addition, the mixture was stirred at 0 °C for 2 h. The reaction mixture was concentrated and purified by silica gel chromatography (2percent EtOAc/petroleum ether) to give 4.3 g of methyl 5-bromo-1H-pyrrole-2-carboxylate 53 as white solid (26percent yield). LCMS:m/z 206.0 [M+H], , tR= 1.50 min
27%
With bromine; iodine In tetrachloromethane; water
A solution of pyrrole-2-carboxylic acid methyl ester (79.9 mmol, 10.0 g) in carbon tetrachloride (300 ml) was heated to 70° C., then treated dropwise with a solution of bromine (99.9 mmol, 126.0 ml) in carbon tetrachloride (200 ml). The reaction was initiated by the addition of iodine (40 mg). After the addition was complete, the reaction was held at 70° C. for 10 min, then cooled to room temperature using an ice bath. The mixture was washed with 10percent aqueous sodium carbonate (100 ml), followed by water (100 ml). The organics were concentrated under reduced pressure and the residue was purified by silica gel chromatography to provide 4.5 g (27percent) of 5-bromo-1H-pyrrole-2-carboxylic acid methyl ester. 1H NMR (CDCl3) δ9.29 (1H, s), 6.80 (1H, dd, J=3.9, 2.7), 6.23 (1H, dd, J=3.8, 2.6), 3.88 (3H, s).
Reference：
[1] Journal of the American Chemical Society, 2006, vol. 128, # 18, p. 6054 - 6055
[2] Chemistry - A European Journal, 2009, vol. 15, # 28, p. 6910 - 6919
[3] Organic and Biomolecular Chemistry, 2013, vol. 11, # 16, p. 2574 - 2577
[4] Patent: WO2017/31213, 2017, A1, . Location in patent: Paragraph 00361
[5] Patent: US2002/6943, 2002, A1,
6
[ 1193-62-0 ]
[ 934-05-4 ]
[ 934-07-6 ]
Reference：
[1] Green Chemistry, 2011, vol. 13, # 1, p. 102 - 108
[2] Journal of Organic Chemistry, 2018, vol. 83, # 16, p. 9250 - 9255
[3] Tetrahedron, 2011, vol. 67, # 22, p. 4048 - 4054
[4] Bioorganic Chemistry, 2012, vol. 44, p. 25 - 34
7
[ 1193-62-0 ]
[ 934-05-4 ]
[ 934-07-6 ]
[ 937-16-6 ]
Reference：
[1] Dalton Transactions, 2013, vol. 42, # 33, p. 11926 - 11940
[2] Green Chemistry, 2011, vol. 13, # 1, p. 102 - 108
[3] Tetrahedron, 2011, vol. 67, # 22, p. 4048 - 4054
8
[ 35302-72-8 ]
[ 934-05-4 ]
[ 934-07-6 ]
Reference：
[1] Green Chemistry, 2011, vol. 13, # 1, p. 102 - 108
[2] Tetrahedron, 2011, vol. 67, # 22, p. 4048 - 4054
9
[ 117067-98-8 ]
[ 934-07-6 ]
Reference：
[1] Canadian Journal of Chemistry, 1990, vol. 68, # 8, p. 1305 - 1308
Preparation of Intermediate 5-Bromo-1H-pyrrole-2-carboxylic Acid Methyl Ester A solution of the preceding intermediate (10.0 g, 79.9 mmol, 1 equiv) in carbon tetrachloride (300 mL) was heated to 70 C., then treated dropwise with a solution of bromine (126.0 mL, 99.9 mmol, 1.25 equiv) in carbon tetrachloride (200 mL). The reaction was initiated by the addition of iodine (40 mg). After the addition was complete, the reaction was held at 70 C. for 10 min, then cooled to 23 C. using an ice bath. The mixture was washed with 10% aqueous sodium carbonate (100 mL), followed by water (100 mL). The volatiles were evaporated, and the residue was purified by silica gel chromatography to obtain 4.5 g (27%) of product: 1H NMR (CDCl3) delta 3.88 (s, 3H), 6.23 (dd, 1H, J=3.8, 2.6), 6.80 (dd, 1H, J=3.9, 2.7), 9.29 (s, 1H).
3
[ 1193-62-0 ]
[ 934-07-6 ]
Yield
Reaction Conditions
Operation in experiment
26%
With N-Bromosuccinimide; In tetrahydrofuran; methanol; at 0℃; for 3.5h;
Synthesis of methyl 5 -bromo- 1H-pyrrole-2-carboxylate (53): Methyl 1H-pyrrole-2-carboxylate (52; lOg, 80 mmol) was dissolved in 800 mL of THF and 400 mL of MeOH. The mixture was cooled to 0 C. NBS (15 g, 8 4 mmol) was added in 5 portions in 1.5 h. After the addition, the mixture was stirred at 0 C for 2 h. The reaction mixture was concentrated and purified by silica gel chromatography (2% EtOAc/petroleum ether) to give 4.3 g of methyl 5-bromo-1H-pyrrole-2-carboxylate 53 as white solid (26% yield). LCMS:m/z 206.0 [M+H], , tR= 1.50 min
4.5 g (27%)
With bromine; iodine; In tetrachloromethane; water;
A solution of pyrrole-2-carboxylic acid methyl ester (79.9 mmol, 10.0 g) in carbon tetrachloride (300 ml) was heated to 70 C., then treated dropwise with a solution of bromine (99.9 mmol, 126.0 ml) in carbon tetrachloride (200 ml). The reaction was initiated by the addition of iodine (40 mg). After the addition was complete, the reaction was held at 70 C. for 10 min, then cooled to room temperature using an ice bath. The mixture was washed with 10% aqueous sodium carbonate (100 ml), followed by water (100 ml). The organics were concentrated under reduced pressure and the residue was purified by silica gel chromatography to provide 4.5 g (27%) of 5-bromo-1H-pyrrole-2-carboxylic acid methyl ester. 1H NMR (CDCl3) delta9.29 (1H, s), 6.80 (1H, dd, J=3.9, 2.7), 6.23 (1H, dd, J=3.8, 2.6), 3.88 (3H, s).
5-Naphthalene-1-yl-1H-pyrrole-2-carboxylic Acid Methyl Ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
2.05 g (81%)
In N,N-dimethyl-formamide;
Argon gas was bubbled 15 min through a solution of <strong>[934-07-6]5-bromo-1H-pyrrole-2-carboxylic acid methyl ester</strong> (10.0 mmol, 2.04 g), 1-naphthylboronic acid (30.0 mmol, 5.16 g), 2M aqueous sodium carbonate (20 ml), and DMF (150 ml). The mixture was then treated with tris(dibenzylidienacetone)dipalladium (0) (0.50 mmol, 0.46 g), and triphenylarsine (2.0 mmol, 0.61 g), then heated to reflux under argon for 12 h. The mixture was partitioned between ethyl acetate (500 ml) and water (150 ml). The organics were filtered through celite, washed with brine (3*50 ml), then concentrated under reduced pressure and the residue was purified by silica gel chromatography to provide 2.05 g (81%) of 5-naphthalen-1-yl-1H-pyrrole-2-carboxylic acid methyl ester. 1H NMR (CDCl3) delta9.37 (1H, s), 8.22-8.17 (1H, m), 8.16-7.89 (2H, m), 7.59-7.50 (4H, m), 7.88 (1H, dd, J=3.9, 2.7), 6.22 (lH, dd, J=3.8. 2.6), 3.88 (3H, s).
5-Bromo-1H-pyrrole-2-carboxylic acid methyl ester (1.49 mmol, 0.30 g, prepared according to the procedure described in Method 4 of Example 2) in NMP (10 ml) was treated with triphenylarsine (0.30 mmol, 91 mg), tris(dibenzylideneacetone) dipalladium(0) (0.07 mmol, 68 mg), and 4-(trimethylstannyl)-isoquinoline (2.22 mmol, 0.65 g), then heated to reflux under an argon atmosphere overnight. The resulting mixture was concentrated under reduced pressure, then purified by silica gel chromatography to provide 0.21 g (55%) of 5-isoquinolin-4-yl-1H-pyrrole-2-carboxylic acid methyl ester. 1H NMR (CDCl3) delta9.81 (1H, br s), 9.35 (1H, s), 8.66 (1H, s), 8.31 (1H, d, J=8.5), 8.10 (1H, d, J=8.1), 7.91 (1H, t, J=15.2), 7.79 (1H, t, J 15.2), 7.11 (1H, dd, J=3.8, 2.5), 6.64 (1H, dd, J=3.7, 2.7), 3.90 (3H, s).
With Ascophyllum nodosum vanadate(V)-dependent bromoperoxidase I; dihydrogen peroxide; sodium bromide; In water; tert-butyl alcohol; at 23℃; for 24h;pH 6.2;aq. buffer; Enzymatic reaction;
General procedure: A solution of H2O2 (3×2.0 mL, 0.825 M) and NaBr (3×154.4 mg, 1.50 mmol) in MES-buffer (500 mM, pH 6.2) was added every day with a syringe pump (8 h, 0.004 mL/min) to a solution of substrate 1 (1.50 mmol) and VBrPO(AnI) (34.6 UT, 0.032 mmol%) in MES-buffer (500 mM, pH 6.2, 20.0 ml) and tBuOH (6.6 mL) [for: 1f 3× H2O2 (2.0 mL, 0.511 M) and NaBr (95.7 mg, 0.93 mmol) in MES-buffer 500 mM to a solution of 1f (0.93 mmol) and VBrPO(AnI) (21.5 UT, 0.032 mmol%) in MES-buffer (500 mM, pH 6.2, 10.1 ml) and tBuOH (4.1 mL)]. The reaction mixture was stirred at 23 C for 3 days. The aqueous layer was extracted with Et2O (3×20 mL). Combined organic extracts were dried (MgSO4). The solvent was removed under reduced pressure (14 mbar, 40 C) to afford a product mixture, which was analyzed by 1H NMR and GC, using pentachlorobenzene (1H NMR) as an internal standard in comparison to spectral data from authentic references. New compounds were purified via column chromatography and fully characterized. pH and bromoperoxidase activity (triiodide assay) were determined from the aqueous layer.
With vanadate-dependent bromoperoxidase II from Ascophyllum nodosum; dihydrogen peroxide; sodium bromide; In tert-butyl alcohol; at 23℃; for 44h;pH 6.2;Enzymatic reaction;
A solution of H2O2 (2.0 mL, 0.825 M) and NaBr (170 mg, 1.65 mmol) in MES-buffer (500 mM, pH 6.2) was added with a syringe pump (20 h, 1.67 muL/min) to a solution of substrate 4 (0.75 mmol) and VBrPO(AnII) (546 muL, 34.6 UT, 63 mumol%) in MES-buffer (500 mM, pH 6.2, 10.0 mL) and tBuOH (3.3 mL). The reaction mixture was stirred at 23 C for 24 h. The aqueous layer was extracted with Et2O (4 × 10 mL). Combined organic extracts were dried (MgSO4). The solvent was removed under reduced pressure (40 mbar, 40 C) to afford a product mixture which was analyzed by 1H NMR (pentachlorobenzene as internal standard) and GC (Supplementary Material). Final pH and bromoperoxidase activity (triiodide assay) were determined from the aqueous layer.
With Ascophyllum nodosum vanadate(V)-dependent bromoperoxidase I; dihydrogen peroxide; sodium bromide; In water; tert-butyl alcohol; at 23℃; for 24h;pH 6.2;aq. buffer; Enzymatic reaction;
General procedure: A solution of H2O2 (3×2.0 mL, 0.825 M) and NaBr (3×154.4 mg, 1.50 mmol) in MES-buffer (500 mM, pH 6.2) was added every day with a syringe pump (8 h, 0.004 mL/min) to a solution of substrate 1 (1.50 mmol) and VBrPO(AnI) (34.6 UT, 0.032 mmol%) in MES-buffer (500 mM, pH 6.2, 20.0 ml) and tBuOH (6.6 mL) [for: 1f 3× H2O2 (2.0 mL, 0.511 M) and NaBr (95.7 mg, 0.93 mmol) in MES-buffer 500 mM to a solution of 1f (0.93 mmol) and VBrPO(AnI) (21.5 UT, 0.032 mmol%) in MES-buffer (500 mM, pH 6.2, 10.1 ml) and tBuOH (4.1 mL)]. The reaction mixture was stirred at 23 C for 3 days. The aqueous layer was extracted with Et2O (3×20 mL). Combined organic extracts were dried (MgSO4). The solvent was removed under reduced pressure (14 mbar, 40 C) to afford a product mixture, which was analyzed by 1H NMR and GC, using pentachlorobenzene (1H NMR) as an internal standard in comparison to spectral data from authentic references. New compounds were purified via column chromatography and fully characterized. pH and bromoperoxidase activity (triiodide assay) were determined from the aqueous layer.
Step 1: To a solution of <strong>[934-07-6]methyl 5-bromopyrrole-2-carboxylate</strong> (340 mg, 1.7 mmol) in dry DMF (8 mL) was added sodium hydride (60% dispersion in mineral oil, 75 mg, 1 .9 mmol) portionwise under nitrogen. After 1 hour at 0 C a solution of 2-bromo-1-(4- methoxyphenyl)ethanone (500 mg, 2.2 mmol) in DMF (4 mL) was added. The resulting yellow solution was then stirred at room temperature for 2.5 hours. Saturated aqueous solution of NH4CI (30 mL) was added and the mixture extracted with EtOAc (100 mL). The organic layer was washed with brine (35 mL), dried (MgS04), filtered and concentrated in vacuo to give a liquid that was purified by flash chromatography (Biotage SP4, 40 g silica cartridge, 0 to 50% EtOAc gradient in hexanes) to give methyl 5-bromo-1 -[2-(4- methoxyphenyl)-2-oxoethyl]-1 H-pyrrole-2-carboxylate as a white solid (525 mg, yield 88%). 1H-NMR (400 MHz, CDCI3): delta 3.73 (s, 3 H), 3.90 (s, 3H), 5.89 (s, 2H), 6.33 (d, 1 H, J 4.1 Hz), 6.99-7.02 (m, 2H), 7.05 (d, 1 H), 7.99-8.02 (m, 2H).
69%
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;
A mixture of ethyl 5-bromo-lH-pyrrole-2-carboxylate (0.13 g, 0.64 mmol), 2-bromo- l-(4-methoxyphenyl)ethanone (160 mg, 0.69 mmol) and potassium carbonate (132 mg, 0.95 mmol) in N,N-dimethylformamide (4 mL) was stirred at room temperature overnight. At this time, the light brown reaction mixture was quenched with water. The resulting precipitate was collected by filtration and dried in vacuo. The resulting solid was dissolved in methylene chloride, concentrated in vacuo and then triturated with diethyl ether. The resulting solid was collected by filtration and dried in vacuo to afford 5-bromo-l-[2-(4-methoxy-phenyl)-2-oxo- ethyl]- lH-pyrrole-2-carboxylic acid methyl ester (155 mg, 69%) as light brown solid. 1H NMR (chloroform-;/) delta ppm 8.00 (d, J= 8.8 Hz, 2H), 6.96 - 7.07 (m, 3H), 6.85 (d, J= 1.8 Hz, 1H), 5.71 (s, 2H), 3.91 (s, 3H), 3.75 (s, 3H).
5-bromo-1-[2-oxo-2-(4-trifluoromethylphenyl)-ethyl]-1H-pyrrole-2-carboxylic acid methyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
64%
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;
A solution of 2-bromo-1-(4-(trifluoromethyl)phenyl)ethanone (160 mg, 0.59 mmol), 2-bromo-1-(4-(trifluoromethyl)phenyl)ethanone (160 mg, 0.59 mmol,) and potassiumcarbonate (100 mg, 0.72 mmol,) in N,N-dimethylformamide (3 mL) was stirred at room temperature overnight. The reaction mixture was quenched with water and was extracted with diethyl ether. The organic layers were combined, dried over sodium sulfate, filtered and concentrated in vacuo. The remaining brown oil was purified by flash chromatography (12 g column, 0-15%) ethyl acetate/hexanes) to afford 5-bromo- 1 -[2-oxo-2-(4-trifluoromethyl-phenyl)-ethyl]-1H-pyrrole-2-carboxylic acid methyl ester (125 mg, 64%) as light yellow solid. 1H NMR (chloroform-d) oe ppm 8.13 (d, J= 8.0 Hz, 2H), 7.82 (d, J= 8.3 Hz, 2H), 7.05 (d, J 1.8 Hz, 1H), 6.87 (d, J 1.8 Hz, 1H), 5.73 (s, 2H), 3.75 (s, 3H).
methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
97%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 4h;
1003621 Synthesis of methyl 5-(4,4,5, 5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1H-pyrrole-2-carboxylate (54): A mixture of <strong>[934-07-6]methyl 5-bromo-1H-pyrrole-2-carboxylate</strong> (53; 1.5 g, 7.3 mmol), 4,4,4,4,5,5,5?, 5?-octamethyl-2,2?-bi( 1,3 ,2-dioxaborolane) (2.7 g, 10.9 mmol), Pd(dppf)C12 (512 mg, 0.7 mmol) and KOAc (1.4 g, 14.6 mmol) in dioxane (100 mL) was degassed and heated at 100C for 4 h. After cooling down to room temperature, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure and purified by silica gel chromatography (30% EtOAc/petroleum ether) to give 1.2 g of methyl 5-(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1H-pyrrole-2-carboxylate 54 as white solid (97% yield). LCMS: m/z 252.1 [M+H], , tR= 1.68 min
(E)-3-(6-aminopyridin-3-yl)-N-((5-(4-(4,4-difluoropiperidine-1-carbonyl)-4’‘-fluoro-[1,1’:3’,1"-terphenyl]-4’-yl)-1H-pyrrol-2-yl)methyl)acrylamide[ No CAS ]
methyl 5-bromo-4-[phenyl (acetyloxy)-lambda3-iodanyl]-1H-pyrrole-2-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
88%
With acetic acid; at 20℃; for 18h;Inert atmosphere;
Methyl 5-bromo-4-[phenyl (acetyloxy)-lambda3-iodanyl]-1H-pyrrole-2-carboxylate To a solution of <strong>[934-07-6]methyl 5-bromo-1H-pyrrole-2-carboxylate</strong> (588 mg, 2.88 mmol) in acetic acid (10 mL) was added (acetyloxy)(phenyl)-lambda3-iodanyl acetate (1.11 g, 3.45 mmol) at room temperature. The resulting solution was stirred for 18 h at room temperature. When the reaction was done, the reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography eluting with DCM/MeOH/AcOH (80:20:5 ratio) to yield methyl 5-bromo-4-[phenyl (acetyloxy)-lambda3-iodanyl]-1H-pyrrole-2-carboxylate as a yellow solid (1.19 g, 88%). MS: m/z=408.0 [M+H]+.
methyl 5-bromo-1-(cyclopropylmethyl)-1H-pyrrole-2-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
89%
In N,N-dimethyl-formamide; at 30℃; for 8h;Inert atmosphere; Sealed tube;
Methyl 5-bromo-1-(cyclopropylmethyl)-1H-pyrrole-2-carboxylate (EV-AS5711- 002)- Step 1 To a solution of <strong>[934-07-6]methyl 5-bromo-1H-pyrrole-2-carboxylate</strong> (CAS 934-07-6, 500 mg, 2.45 mmol) in anhydrous DMF (5 ml) was added sodium hydride (60%, 150 mg, 3.75 mmol). To this solution was added (bromomethyl)cyclopropane (350 mul, 3.61 mmol) and the mixture stirred under nitrogen at 30 C in a sealed tube for 8h. The reaction mixture was concentrated, quenched with methanol and purified by flash column chromatography (0-50% ethyl acetate/heptane) to afford 566 mg (89%) of methyl 5-bromo-1-(cyclopropylmethyl)-1H-pyrrole- 2-carboxylate (EV-AS5711-002) as a yellow oil. LCMS (method D): retention time 1.44 min, M/z = 258/260 (M + 1).
methyl 1-benzyl-5-bromo-1H-pyrrole-2-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
99%
Methyl 1-benzyl-5-bromo-1H-pyrrole-2-carboxylate (EV-AU7290-001)- Step 1 To a solution of DIAD (1.03 ml, 4.90 mmol) in dry THF (5 ml) under nitrogen at - 20C was added a solution of triphenylphosphine (1.30 g, 4.90 mmol) in dry THF (10 ml). The mixture was stirred for 30 minutes and a solution of <strong>[934-07-6]methyl 5-bromo-1H-pyrrole-2-carboxylate</strong> (CAS 934-07-6, 500 mg, 2.45 mmol) in dry THF (5 ml) was added. The mixture was stirred at - 20C for a further 30 minutes and phenylmethanol (CAS 100-51-6, 0.38 ml, 3.67 mmol) in dry THF (5 ml) was added dropwise at -20C and the reaction mixture was allowed to warm to room temperature and stirred for 62h. The solvent was removed in vacuo and the crude material was purified by flash column chromatography (5 - 30% ethyl acetate/heptane) to obtain 730 mg (99%) of methyl 1-benzyl-5-bromo-1H-pyrrole-2-carboxylate (EV-AU7290-001) as a pale yellow oil. LCMS (method D): retention time 1.32min, M/z = 294/296 (M + 1).
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,4-dioxane; water; for 2h;Reflux; Inert atmosphere;
ompound 22 is (1.16 g, 5.25mmol), 23 is (710mg, 3.5mmol), Pd (PPh3. 3)2CI2(491 mg,0.7 mmol) were sequentially added to a dioxane (30mL), the state under an argon atmosphere was added K2CO.'s. 3(2.9 g of, 21 mmol) in water(10.5 mL) was heated refluxed for 2h.After completion of the reaction by TLC, the reaction mixture was diluted with 300 mL of ethyl acetate, washed with water, washed withsaturated sodium chloride, dried and evaporated to dryness to give 24 (578 mg, 64%).
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In ethanol; water; toluene; at 130℃; for 0.5h;Microwave irradiation;
Methyl 5-bromo-1 H-pyrrole-2-carboxylate (232 mg), 4-tert-butylPhenylboronic acid (302 mg), cesium carbonate (480 mg), tetrakis (triphenylphosphine) palladium (0) (40 mg), methanol (1.0 mL), toluene (1.0 mL) and water (1. 0 mL) was stirred under microwave irradiation at 130 C. for 30 minutes. The reaction solution was diluted with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane: ethyl acetate = 100: 0 to 70:30) to give the title compound (138 mg).
methyl 5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrole-2-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
96%
General procedure: First, t-BuOK (330 mg, 2.94 mmol) was added to a solution of bromopyrroles (500 mg, 2.45 mmol) in anhydrous DMF (5 mL) in an ice-bath, and the mixture was stirred for 0.5 h. SEM-Cl (449 mg,2.7 mmol) was added to the resulting mixture. The reaction mixture was stirred at rt for 2 h, and then quenched with H2O. The mixture was extracted with EtOAc (15 mL 3), and the combined organic layer was washed with sat. NaHCO3 and brine, dried with Na2SO4, and concentrated. The product was obtained by flash chromatography (EtOAc in PE = 3%).
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