* 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.
2: 6-Bromo-3H-oxazolo[4,5-b]pyridin-2-one (21.5 g, 100 mmol) was suspended in NaOH solution (2N, 250 mL, 500 mmol). The mixture was refluxed overnight and a clear solution was obtained. After cooling to room temperature, the reaction solution was neutralized to pH ~7. A lot of CO2 was released and also precipitate was observed. The product was filtered, washed with water, and dried under high vacuum to provide 2-amino-5-bromo-pyridin-3-ol as an off-white solid (17.8 g, 98percent yield).
6-Bromo-3H-oxazolo[4,5-b]pyridin-2-one (21.5 g, 100 mmol) was suspended in NaOH solution (2N, 250 mL, 500 mmol). The mixture was refluxed overnight and a clear solution was obtained. After cooling to room temperature, the reaction solution was neutralized to pH ~7. A lot of C02 was released and also precipitate was observed. The product was filtered, washed with water, and dried under high vacuum to provide 2-amino-5-bromo-pyridin-3-ol as an off-white solid (17.8 g, 98percent yield).
80%
Stage #1: Heating / reflux Stage #2: With hydrogenchloride In water
To a solution of 6-bromo-3H-oxazolo[4,5-.pound.]pyridin-2-one (28.0 g, 130 mmol) in MeOH (280 mL) was added a solution of NaOH (28.1 g, 703 mmol) in water (280 mL). The mixture was heated to reflux overnight. The organic solvent was removed in vacuo and the aqueous mixture was adjusted to pη 5-6 with 12 M HCl. The resulting precipitate was isolated by filtration, washed with Et2ψ and dried under vacuum at 50 °C overnight to give the title compound (19.6 g, 80percent) as a gray solid: 1H NMR (500 MHz, DMSO-cfc) δ 10.1 (s, IH), 7.46 (d, J= 1.5 Hz, IH), 6.88 (s, IH), 5.70 (s, 2H); ESI MS m/z 190 (M + H)+.; To a suspension of 6-bromo-3H-oxazolo[4,5-]pyridin-2-one (20.0 g, 93.0 mmol) in methanol (200 mL) was added NaOH (20.0 g, 500 mmol) in H2O (200 mL) and the mixture was heated to reflux overnight. After cooling, methanol was removed in vacuo. The aqueous residue was acidified with 3N HCl to pH 5-6. The resulting precipitate was collected by filtration, and dried overnight under vacuum at 45 0C to give the title compound as a tan solid (16.4 g, 93percent): 1H NMR (300 MHz, DMSO-^) δ 10.03 (s, IH), 7.47 (d, J= 2.0 Hz, IH), 6.93 (d, J= 2.0 Hz, IH), 5.72 (s, 2H); ESI MS m/e 188 (M + H)+.
80%
Stage #1: at 100℃; for 6 h; Stage #2: With hydrogenchloride In water at 5℃;
[00104] As shown in step 4-iii of Scheme 20, Compound 1012 (34 g, 158.1 mmol) was diluted with 10percent NaOΗ(aq) (500 mL), and the resulting mixture was stirred at 100 0C for 6 h. The reaction was cooled to 5 0C, and 6 N HCl was added until a precipitate formed (ca. pH 10). The solid was collected in a fritted funnel, washed with water (200 mL), and dried under vacuum to afford 2-amino-5-bromo-3-hydroxypyridine (Compound 1013, 24.0 g, 80percent yield) as a tan solid: ESMS (M+H) 189, 191; 1H NMR (DMSO-d6) δ 7.5 (s, IH), 6.9 (s, IH), 5.7 (br, 2H).
80%
Stage #1: With sodium hydroxide In water at 100℃; for 6 h; Stage #2: With hydrogenchloride In water
As shown in step 4-iii of Scheme 20, Compound 1012 (34 g, 158.1 mmol) was diluted with 10percent NaOΗ(aq) (500 mL), and the resulting mixture was stirred at 100 0C for 6 h. The reaction was cooled to 5 0C, and 6 N HCl was added until a precipitate formed (ca. pH 10). The solid was collected in a fritted funnel, washed with water (200 mL), and dried under vacuum to afford 2-amino-5-bromo-3-hydroxypyridine (Compound 1013, 24.0 g, 80percent yield) as a tan solid: ESMS (M+H) 189, 191; 1H NMR (DMSO-d6) δ 7.5 (s, IH), 6.9 (s, IH), 5.7 (br, 2H).
Reference：
[1] Archiv der Pharmazie, 2011, vol. 344, # 3, p. 158 - 164
7
[ 24016-03-3 ]
[ 39903-01-0 ]
Reference：
[1] Archiv der Pharmazie, 2011, vol. 344, # 3, p. 158 - 164
8
[ 106840-72-6 ]
[ 39903-01-0 ]
Reference：
[1] Patent: WO2016/97918, 2016, A1,
9
[ 874-24-8 ]
[ 39903-01-0 ]
Reference：
[1] Patent: US4022897, 1977, A,
10
[ 100-39-0 ]
[ 39903-01-0 ]
[ 754230-78-9 ]
Reference：
[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 18, p. 6342 - 6363
11
[ 59154-46-0 ]
[ 39903-01-0 ]
[ 894852-01-8 ]
Yield
Reaction Conditions
Operation in experiment
84%
With potassium carbonate In acetone for 18 h; Heating / reflux
a) 7-Bromo-2,2-dimethyl-4H-pyrido[3,2-] [ 1 ,4]oxazin-3 -one; To a mixture of 2-amino-5-bromopyridin-3-ol (0.500 g, 2.64 mmol) and K&2CO3 (1.09 g, 7.93 mmol) in acetone (11.0 niL) was added ethyl bromoisobutyrate (0.50 mL, 3.4 mmol). The solution was stirred under N2 for 18 h and then heated to reflux. After 18 h, the solution was cooled and concentrated. The light-pink, sweet-smelling solid was dissolved in CH2Cl2 (50 mL) and MeOH (5 mL). The solution was diluted with H2O (150 mL) and then washed with CH2Cl2 (3 x 75 mL). The combined organic layers were washed with brine (2 x 100 mL), dried (Na2SO4) and concentrated to yield the title compound (0.57 g, 84percent) as an off-white solid: 1H NMR (300 MHz, DMSO-J,*) δ 11.39 (s, IH), 8.03 (d, J=1.2 Hz, IH), 7.66 (d, 0.9 Hz, IH), 1.43 (s, 6H).
[00188] 2-Amino-3-hydroxy-5-bromopyridine (Heterocycles, 1995, 41, 2799) (124 mg, 0.65 mmol) was dissolved in EtOH (3 niL) and added chloroacetaldehyde (0.2 niL, 1.3 mmol, 50percent in water) and the resulting solution heated at 60 °C overnight. The solvents were then removed and the solids were crystallized from acetone to give 6-bromoimidazo[l,2-a]pyridin-8-ol hydrochloride (151 mg, 92percent).
92%
at 60℃;
2-Amino-3-hydroxy-5-bromopyridine (Heterocycles, 41 :2799 (1995)) (124 mg, 0.65 mmol) was dissolved in EtOH (3 niL) and added chloroacetaldehyde (0.2 mL, 1.3 mmol, 50percent in water) and the resulting solution heated at 60 0C overnight. The solvents were then removed and the solids were crystallized from acetone to give 6-bromoimidazo[l,2-a]pyridin-8-ol hydrochloride (151 mg, 92percent)
Preparation 56-Bromo-oxazolo[4,5-b]pyridine[00122] 2-Amino-5-bromo-3-hydroxypyridine (200 mg, 1.06 mmol) is dissolved in 3 ml of triethylortoformate and a catalytic amount of p-toluenesulfonic acid is added. The mixture is heated to reflux for 5 h, then cooled, diluted with DCM and washed with saturated sodium bicarbonate solution. The organic phase is dried over anhydrous sodium sulfate and evaporated to dryness. The residue is purified by flash column chromatography to afford 212 mg (60percent) of the title compound.
With triethylamine In dichloromethane at 20℃; for 18 h;
Example 1 The preparation of 5-bromo-3-hydroxy-2-tert-butyloxycarbonylamino pyridine (0038) To a solution of 2-amino-3-hydroxy-5-bromopyridine (10.0 g, 53.0 mmol) and Et3N (10 mL, 71.8 mmol) in dichloromethane (100 mL) was added Boc2O (12.7 g, 58.4 mmol). The mixture was stirred at room temperature for 18 h and continued to stir for 30 min after the addition of 150 ml water. The reaction mixture was filtrated off through celite. The organic layer was separated and the aqueous layer was extracted with 150 dichloromethane. The combined organic layers were washed with saturated NaCl aqueous solution (2×100 mL) and then dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the obtained residue was triturated in hexane (100 mL), filtrated, and dried under vacuum to afford 15.0 g 5-bromo-3-hydroxy-2-tert-butyloxycarbonylamino pyridine as a white solid, with a yield of 98.0percent. (0039) 1H NMR (400 MHz, CDCl3): δ 7.98 (d, J=2.0 Hz, 1H), 7.58 (d, J=2.0 Hz, 1H), 4.67 (brs, 2H), 1.56 (s, 9H); 1C NMR (100 MHz, CDCl3): δ 150.4, 150.1, 145.3, 133.5, 131.5, 106.5, 85.0, 27.6.
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 120℃; for 0.333333h;Microwave irradiation;
To a suspension of <strong>[39903-01-0]2-amino-5-bromopyridin-3-ol</strong> (1.42 g, 7.51 mmol) in THF (40 mL) was added methyl 2,2-dimethyl-3-hydroxypropionate (1.2 mL, 9.0 mmol) and triphenyl phosphine (2.36 g, 9.00 mmol). The mixture was cooled to 0 0C, then treated with diethyl diazodicarboxylate (1.70 g, 9.75 mmol). The mixture was heated in microwave at 120 0C for 20 min. The solvent was concentrated, and the residue was purified by chromatography (silica gel, hexanes/EtOAc, 75:25 to 60:40) to give the title compound (0.88 g, 39percent) as a white solid: 1H NMR (300 MHz, CDCl3) delta 7.73 (d, J= 2.1 Hz, IH), 7.02 (d, J= 2.1 Hz, IH), 4.65 (br s, 2H), 3.96 (s, 2H), 3.71 (s, 3H), 1.34 (s, 6H); ESI MS m/e 303 (M + H)+. b) 3-Bromo-7,7-dimethyl-6,7-dihydro-9H-5-oxa-l,9-diaza-benzocyclohepten-8- one
With caesium carbonate; In N,N-dimethyl-formamide; at 60℃; for 17h;
To a stirred solution of 28-6 (1.15 g, 3.78 mmol) and <strong>[39903-01-0]2-amino-5-bromo-pyridin-3-ol</strong> (3.78 g, 3.78 mmol) in DMF (8 mL, 0.5 M) was added CS2CO3 (1.23 g, 3.78 mmol). The reaction mixture was stirred for 17 hours at 60 °C. The reaction was cooled to room temperature and water (20 mL) was added. The solution was extracted with EtOAc (4 x 20 mL), dried with Na2SO4 and removal of the solvent in vacuo. The crude reaction was purified by silica gel column chromatography to afford a light yellow solid 28-7 (600 mg, 41percent yield). 1H NMR (CDCI3, 400 MHz) 87.69 (s, 1H), 7.04 (t, 7.04), 6.01 (m, 1H), 4.80 (bs, 2H), 1.82(d, 3H).
t-butyl 2-(6-amino-3-bromo-5-hydroxy-2-pyridylazo)-5-phenyl-3-thenoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sulfuric acid; sodium nitrite; In pyridine; water;
D. t-Butyl 2-(6-amino-3-bromo-5-hydroxy-2-pyridylazo)-5-phenyl-3-thenoate A solution of t-butyl 2-amino-5-phenyl-3-thenoate (8.26 g; 0.03 mole) in 2:5 acid (120 ml) (see Example 1) was chilled to -2° C. and concentrated sulfuric acid (5 ml) was added at such a rate that the temperature did not exceed 2° C.; a solution of sodium nitrite (2.16 g) in water (5 ml) was added dropwise below 2° C. The resulting diazonium solution was stirred at -2° C. to +2° C. for 45 minutes, then added in a slow stream with magnetic stirring to a cold (below 5° C.) solution of <strong>[39903-01-0]2-amino-5-bromo-3-pyridinol</strong> (Example 2-L) (5.67 g; 0.03 mole) in pyridine (30 ml) and 2:5 acid (90 ml). The dye solution was stirred at 0° to 5° C. for 1.5 hours, then the cooling bath was removed and the mixture stirred for an additional 30 minutes. After drowning in cold water (2.5 liters), the dye was collected on a filter, washed with water and dried to yield 14.7 g of material with only traces of impurities.
B. The 2-amino-5-bromo-3-pyridinol is prepared by dissolving 110.0 g of 2-amino-3-pyridinol in 250 ml of 95percent ethanol. The solution is cooled to about 5° C. and at that temperature is treated with 160 g of liquid bromine during 2 hours. The mixture is stirred for 1 hour after the addition is completed and then concentrated to give 170.6 g of 2-amino-5-bromo-3-pyridinol.
With potassium hydroxide; In tetrahydrofuran; diethylene glycol dimethyl ether; cyclohexane; ethylene glycol; ethyl acetate;
EXAMPLE 5 A mixture of 5 parts of 2-amino-3-chloro-5-bromopyridine, 20 parts of potassium hydroxide (85percent), 3 parts of diethylene glycol dimethyl ether, 0.3 part of copper-bronze and 40 parts of glycol is stirred under nitrogen for 7 hours at 170°-175° C. After cooling, the dark-coloured solution is neutralised with concentrated hydrochloric acid, saturated with sodium chloride and extracted twice in the warm state with ethyl acetate/tetrahydrofuran (9:1). The organic layer is extracted by shaking with a saturated sodium chloride solution; the ethyl acetate phase is then filtered through Hyflo, dried with magnesium sulphate and purified with active charcoal. The clear yellow solution is concentrated almost to dryness and chromatographed through a short silica-gel column with ethyl acetate/cyclohexane (2:1). The yield is 2 parts of 2-amino-3-hydroxy-5-bromopyridine, m.p. 204°-207° C. (44.1percent of theory).
With potassium carbonate; sodium iodide; In acetone;Heating / reflux;
5-Bromo-3-(pyridine-2-ylmethoxy)-pyridin-2-ylamine To a suspension of <strong>[39903-01-0]2-amino-5-bromo-pyridin-3-ol</strong> (2.00 g, 10 mmol) in acetone (80 mL) was added to 2-chloromethyl-pyridine hydrochloride (2.24 g, 13.7 mmol), K2CO3 (4.38 g, 31.7 mmol) and NaI (4.74 g, 31.7 mmol). The mixture was heated to reflux overnight. After cooling, the mixture was diluted with water and then extracted with EtOAc (3x). The combined organics were washed with brine, dried (Na2SO4) and concentrated. Purification by column chromatography (silica gel, hexanes/EtOAc, 1 :4) gave the title compound (830 mg, 27percent) as a brown oil: 1H NMR (300 MHz, delta 8.61-8.57 (m, IH), 7.88-7.84 (m, IH), 7.66 (d, J = 8.1 Hz, IH), 7.60 (d, J= 1.8 Hz, IH), 7.35 (dd, J= 7.5, 3.0 Hz, IH), 7.28 (d, J= 2.1 Hz, IH) <n="94"/>6.06 (s, 2H), 5.21 (s, 2H); ESI MS m/z 280 (M + H)+.
With potassium carbonate; sodium iodide; In acetone;Heating / reflux;
00 suspension of <strong>[39903-01-0]2-amino-5-bromo-pyridin-3-ol</strong> (1.00 g, 5.29 mmol) in acetone (40 mL) was added to a solution of 3-chloromethylpyridine hydrochloride (1.12 g, 6.87 mmol), K2CO3 (2.19 g, 15.8 mmol) and NaI (2.37 g, 15.8 mmol). The mixture was heated to reflux overnight. After cooling, the mixture was dissolved in water and extracted with EtOAc (3x). The combined organics were washed with brine, dried and concentrated. Purification by column chromatography (silica gel, hexanes/EtOAc, 1 :4) gave the title compound (430 mg, 29percent) as a brown oil: 1H NMR (300 MHz, DMSO-^) delta 8.71 (d, J= 1.8 Hz, IH), 8.55 (d, J= 3.0 Hz IH), 7.96-7.92 (m, IH), 7.60 (d, J= 3.0 Hz, IH), 7.45-7.35 (m, IH), 7.34 (d, J= 3.0 Hz, IH), 6.04 (br s, 2H), 5.20 (s, 2H); ESI MS m/z 280 (M + H)+.
To a solution of <strong>[39903-01-0]2-amino-5-bromopyridin-3-ol</strong> (1.89 g, 10.0 mmol) in 1,4-dioxane (20 mL) was added acetic anhydride (4.7 mL, 50 mmol) and the mixture was heated to reflux for 20 h. After cooling, the solvent was removed in vacuo. Purification by column chromatography <n="97"/>(silica gel, hexanes/EtOAc, 70:30 to 50:50) gave the title compound (2.30 g, 73percent) as a white solid: 1H NMR (300 MHz, CDCl3) delta 8.52 (d, J= 2.1 Hz, IH), 7.87 (d, J= 2.1 Hz, IH), 2.30 (s, 6H), 2.29 (s, 3H); ESI MS m/e 315 (M + H)+.
Synthesis Example 7 Synthesis of Exemplified Compound No. 32 2-amino-5-bromopyridin-3-ol [19] was synthesised by the method described in Heterocycles, 55, 1329 (2001). Then, 6-bromo-2-phenyl-oxazolo[4,5-b]pyridine [21] (pale yellow crystal) was obtained from [19] and benzoic acid [20] in 84percent yield. The following compounds were placed in a 300-ml three-necked flask, and the mixture was stirred under nitrogen atmosphere at room temperature. During the stirring, an aqueous solution of 3 g of sodium carbonate in 30 ml of water was added dropwise to the mixture. 1.95 g (7.09 mmol) of 2-amino-5-bromopyridine-3-ol [19] 1.50 g (3.36 mmol) of a 9,9-dimethylfluorene-2,7-diboronic acid pinacol ester [4] 75 ml of toluene and 38 ml of ethanol Next, 0.39 g (0.34 mmol) of tetrakis(triphenylphosphine)palladium(0) was added to the mixture. After the mixture was stirred at room temperature for 10 minutes, the temperature of the mixture was increased to 78° C., and the mixture was stirred under heating and reflux for 4 hours. The reaction liquid was filtrated, and the resultant crude product was dissolved in 300 ml of chloroform at 70° C. The solution was purified with a silica gel column (toluene/acetic ether 5/1), whereby 1.53 g of Exemplified Compound No. 32 (white crystal) was obtained (78percent yield).
41
[ 39903-01-0 ]
[ 75-03-6 ]
5-bromo-3-ethoxypyridin-2-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
59%
With sodium hydroxide; In dichloromethane; water; at 20℃; for 16h;
To a stirred solution of <strong>[39903-01-0]2-amino-5-bromopyridine-3-ol</strong> (25 g, 132.9 mmol) in dichloromethane (150 niL) was added iodoethane (41.43 g, 265 mmol), aliquat (7.5 g) and 40percent aqueous sodium hydroxide (150 mL) at RT, followed by stirring for 16 h. The reaction mixture was diluted with water (150 mL) and extracted with dichloromethane (2 x 300 mL). The combined organic layers were concentrated to dryness in vacuo and the resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 20percent ethyl acetate in hexane) affording 5-bromo-3-ethoxypyridin-2-amine as and off white solid (17 g, 59percent): NMR (300 MHz, DMSO-d6) delta 7.58 (s, 1H), 7.18 (s, 1H), 5.85 (s, 2H), 4.2 - 3.8 (m, 2H), 1.20 - 1.40 (m, 1H), 0.65 - 0.55 (m, 2H).
59%
With sodium hydroxide; In dichloromethane; water; at 20℃; for 16h;
Preparative Example 2 Step 1: 5-bromo-3-ethoxypyridin-2-amine To a stirred solution of <strong>[39903-01-0]2-amino-5-bromopyridine-3-ol</strong> (25 g, 132.9 mmol) in dichloromethane (150 niL) was added iodoethane (41.43 g, 265 mmol), aliquat (7.5 g) and 40percent aqueous sodium hydroxide (150 niL) at RT, followed by stirring for 16 h. The reaction mixture was diluted with water (150 mL) and extracted with dichloromethane (2 x 300 mL). The combined organic layers were concentrated to dryness in vacuo and the resulting residue was purified by column chromatography (silica gel, 100- 200 mesh, 20percent ethyl acetate in hexane) affording 5-bromo-3-ethoxypyridin-2-amine as and off white solid (17 g, 59percent): lU NMR (300 MHz, DMSO-d6) delta 7.58 (s, 1H), 7.18 (s, 1H), 5.85 (s, 2H), 4.2 - 3.8 (m, 2H), 1.20 - 1.40 (m, 1H), 0.65 - 0.55 (m, 2H).
46%
With sodium hydroxide; In dichloromethane; water; at 20℃; for 21h;
00105] As shown in step 4-iv of Scheme 20, Compound 1013 (19.0 g, 100.5 mmol) was dissolved in DCM (90 mL), and iodoethane (9.0 mL, 110.6 mmol), Adogen.(R). 464 (methyltrialkyl(C8-Cio)ammonium chloride, 0.6 g), and 40percent NaOH(aq) (90 mL) were added. The reaction was stirred at RT for 21 h. The DCM layer was separated, and the aqueous layer was diluted with water (100 mL) and extracted with DCM (2 x 100 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified on a silica plug eluting with 40percent ethyl acetate/hexanes to afford 2- amino-5-bromo-3-ethoxypyridine (Compound 1014, 10.0 g, 46percent yield) as a white solid: ESMS (M+H) 217, 219. 1H NMR (DMSO-d6) delta 7.6 (s, IH), 7.1 (s, IH), 5.8 (br, 2H), 4.0 (q, 2H), 1.3 (t, 3H).
46%
With sodium hydroxide; In dichloromethane; water; at 20℃; for 21h;
As shown in step 4-iv of Scheme 20, Compound 1013 (19.0 g, 100.5 mmol) was dissolved in DCM (90 mL), and iodoethane (9.0 mL, 110.6 mmol), Adogen.(R). 464 (methyltrialkyl(C8-Cio)ammonium chloride, 0.6 g), and 40percent NaOH(aq) (90 mL) were added. The reaction was stirred at RT for 21 h. The DCM layer was separated, and the aqueous layer was diluted with water (100 mL) and extracted with DCM (2 x 100 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified on a silica plug eluting with 40percent ethyl acetate/hexanes to afford 2- amino-5-bromo-3-ethoxypyridine (Compound 1014, 10.0 g, 46percent yield) as a white solid: ESMS (M+H) 217, 219. 1H NMR (DMSO-d6) delta 7.6 (s, IH), 7.1 (s, IH), 5.8 (br, 2H), 4.0 (q, 2H), 1.3 (t, 3H).
Preparation 56-Bromo-oxazolo[4,5-b]pyridine[00122] 2-Amino-5-bromo-3-hydroxypyridine (200 mg, 1.06 mmol) is dissolved in 3 ml of triethylortoformate and a catalytic amount of p-toluenesulfonic acid is added. The mixture is heated to reflux for 5 h, then cooled, diluted with DCM and washed with saturated sodium bicarbonate solution. The organic phase is dried over anhydrous sodium sulfate and evaporated to dryness. The residue is purified by flash column chromatography to afford 212 mg (60percent) of the title compound.
PREPARATION 412-[1-(2-Amino-5-bro -pyridin-3-yloxy)-ethyl]-4-fluoro-benzonitrileTo a rapidly stirred mixture of 5-bromo-3-hydroxy-2-amino-pyridine (1.03 g, 5.46 mmol) and tetrabutylammonium bromide (0.026 g, 0.08 mmol, 0.015 eq.) in dichloromethane (6 mL) was added an aqueous solution of sodium hydroxide (7.7M, 4.0 mL, 5.6 eq.). The mixture was stirred for 15 min before a solution of the bromide from preparation 40 (1.37 g, 6.0 mmol, 1.1 eq.) in dichloromethane (6mL) was added and stirring continued for a further 18 hr. The resulting mixture was diluted with dichloromethane (50 mL) and partitioned with water. The organic phase was dried over magnesium sulphate and this mixture filtered. The filtrate was evaporated under reduced pressure. The residue was purified by chromatography on silica gel (300 g) eluting with a gradient of ethyl acetate in heptane (10:90 to 50:50) to give the title compound as a beige solid (1.62 g, 87percent). 1H NMR (400 MHz, CDCI3): delta ppm 1.75 (d, 3H), 4.8 (br s, 2H), 5.6 (q, 1 H), 6.8 (s, 7.1 (m, 1 H), 7.2 (m, 1 H), 7.7 (m, 2H)
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