5-hydroxypentan-2-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compound was prepared from 2,6-dichloropyridine-3,5-dicarbonitrile, 5-hydroxypentan-2-one, and benzo[c][1,2]oxaborole-1,5(3H)-diol in a similar manner to that of D230. 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 1.7-1.73 (m, 2H), 2.04 (s, 3H), 2.35 (t, J=5.4 Hz, 2H), 4.06 (t, J=5.1 Hz, 2H), 5.02 (s, 2H), 7.29 (dd, J=6.3, 1.5 Hz, 1H), 7.39 (d, J=1.2 Hz, 1H), 7.81 (d, J=6.0 Hz, 1H), 8.94 (s, 1H), 9.3 (s, 1H).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compound was prepared from 2,6-dichloropyridine-3,5-dicarbonitrile, 5-hydroxypentan-2-one, and benzo[c][1,2]oxaborole-1,5(3H)-diol in a similar manner to that of D230. 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 1.7-1.73 (m, 2H), 2.04 (s, 3H), 2.35 (t, J=5.4 Hz, 2H), 4.06 (t, J=5.1 Hz, 2H), 5.02 (s, 2H), 7.29 (dd, J=6.3, 1.5 Hz, 1H), 7.39 (d, J=1.2 Hz, 1H), 7.81 (d, J=6.0 Hz, 1H), 8.94 (s, 1H), 9.3 (s, 1H).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compound was prepared from 2,6-dichloro-4-(trifluoromethyl)nicotinamide, 5-hydroxypentan-2-one, and benzo[c][1,2]oxaborole-1,5(3H)-diol in a similar manner to that of D230. 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 1.85-1.88 (m, 2H), 1.93 (s, 3H), 2.95-2.99 (t, J=4.9 Hz, 2H), 3.91-3.94 (t, J=5.4 Hz, 2H), 5.01 (s, 2H), 7.21 (dd, J=6.0, 1.5 Hz, 1H), 7.3 (s, 1H), 7.64 (s, 1H), 7.81 (d, J=6.0 Hz, 1H), 9.26 (s, 1H).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This compound was prepared from 2,6-dichloro-4-(trifluoromethyl)nicotinamide, 5-hydroxypentan-2-one, and benzo[c][1,2]oxaborole-1,5(3H)-diol in a similar manner to that of D230. 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 1.85-1.88 (m, 2H), 1.93 (s, 3H), 2.95-2.99 (t, J=4.9 Hz, 2H), 3.91-3.94 (t, J=5.4 Hz, 2H), 5.01 (s, 2H), 7.21 (dd, J=6.0, 1.5 Hz, 1H), 7.3 (s, 1H), 7.64 (s, 1H), 7.81 (d, J=6.0 Hz, 1H), 9.26 (s, 1H).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 2,6-dichloro-5-cyclopropylnicotinamide (2.00 g, 8.66 mmol) and 5-hydroxypentan-2-one (883 mg, 8.66 mmol) in DMF (30 mL) was added and NaH (416 mg, 10.4 mmol) in portions at 0° C. The mixture was stirred at r.t. overnight, quenched by water, extracted by EtOAc. The separated organics was dried, concentrated and purified by column chromatography (Petroleum ether:EtOAc=10:1˜1:1) to give 6-chloro-5-cyclopropyl-2-(4-oxopentyloxy)nicotinamide (500 mg, 19.4%). was added at 0° C quenched by water extracted by EtOAc The separated organics was dried concentrated purified by column chromatography (Petroleum ether:EtOAc=10:1˜1:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 3-acetyl-1-propanol (3.000 g, 29.37 mmol), tert-butyldimethylsilyl chloride (4.522 g, 30.00 mmol), and imidazole (5.004 g, 73.5 mmol) in DMF (40 mL) was heated at 40° C. for 5 h and was stirred at room temperature for 66 h. Water (60 mL) was added and the product was extracted into EtOAc (4×50 mL). The combined organic extracts were washed with water (2×50 mL), dried over MgSO4, filtered, and concentrated. Purification by flash chromatography (hexanes:EtOAc 9:1) provided the title compound (3.722 g). 1H NMR (400 MHz, CDCl3) δ 3.59 (t, 2H), 2.49 (t, 2H), 2.13 (s, 3H), 1.76 (m, 2H), 0.86 (s, 9H), 0.02 (s, 6H); MS 217 (M+1). the product was extracted into EtOAc (4×50 mL) The combined organic extracts were washed with water (2×50 mL) dried over MgSO4 filtered concentrated Purification by flash chromatography (hexanes:EtOAc 9:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of acetaldehyde N1 -(7-chloroquinazolin-4-yl)p-methoxyphenylhydrazone hydrochloride (3.2g.) and 5-hydroxy-pentane-2-one (1.1g.) in ethanol (60ml.) was refluxed for 18 hours. The mixture was cooled and filtered and the filtrate evaporated in vacuo. The residue was chromatographed on silica gel (100g.) using, as eluant, petroleum ether (b.p. 40° -60° C.) containing an increasing proportion of ether (polarity increased by incremental addition of 10% v/v ether) to give 1-(7-chloroquinazolin-4-yl)-3-(2-hydroxyethyl)-5-methoxy-2-methylindole, m.p. 148°-150° C. The mixture was cooled filtered the filtrate evaporated in vacuo The residue was chromatographed on silica gel (100g.) petroleum ether (b.p. 40° -60° C.) containing an increasing proportion of ether (polarity increased by incremental addition of 10% v/v ether)