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With hypophosphorous acid; sodium nitrite In water at 0 - 20℃; for 0.75 h;
A solution of sodium nitrite (5.28g; 76.5 mmol) in water (17ml) was added drop wise over 5 minutes to a stirred solution of Al.4 (11.3 g; 52 mmol) in hypophosphorous acid (50 wt. percent solution in water, 15OmL) at 0° C to 50C. The reaction mixture was allowed to warm to room temperature and stirred for an additional 40 minutes. The mixture was cooled in an ice bath (0° C to 50C ) and the pH was adjusted to >10 by the addition of aqueous sodium hydroxide (55g in 100 mL of water). The resulting suspension was filtered. The filter cake was rinsed with water and suction dried to afford 9.9 g (97percent) of A1.5 as a PiPLC: 99percent, ret. time = 0.92 min., LC/MS (M+H)+ = 202.06 (204.04, 206.02).
75%
Stage #1: With hypophosphorous acid; sodium nitrite In water at 0 - 20℃; for 2 h; Stage #2: With sodium carbonate In water at 0℃;
A1.5: 4,6-Dichloro-l -methyl- lH-imidazo[4,5-c1pyridine A1.5A solution of sodium nitrite (415 mg; 6 mmol) in 2 ml of water was added drop wise over 5 minutes to a stirred solution of A1.4 (0.87 g; 4 mmol) in 14 ml of 50percent aqueous H3PO2 at 0° C. The reaction mixture was allowed to warm to room temperature over ~2hr. After diluting the reaction mixture with water (250 ml) and re-cooling to 0° C, the ph was adjusted to ~9 by carefully adding solid sodium carbonate. The resulting suspension was filtered. The filter cake was rinsed with water and suction dried to afford 061 g (75percent) of A1.5 as a HPLC: 99percent, ret. time = 0.92 min., LC/MS (M+H)+ = 202.05 (204.04, 206.02).
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 10, p. 2646 - 2649
[2] Patent: WO2006/122137, 2006, A1, . Location in patent: Page/Page column 71
[3] Patent: WO2006/53166, 2006, A1, . Location in patent: Page/Page column 57
With hypophosphorous acid; sodium nitrite; In water; at 0 - 20℃; for 0.75h;Product distribution / selectivity;
A solution of sodium nitrite (5.28g; 76.5 mmol) in water (17ml) was added drop wise over 5 minutes to a stirred solution of Al.4 (11.3 g; 52 mmol) in hypophosphorous acid (50 wt. % solution in water, 15OmL) at 0 C to 50C. The reaction mixture was allowed to warm to room temperature and stirred for an additional 40 minutes. The mixture was cooled in an ice bath (0 C to 50C ) and the pH was adjusted to >10 by the addition of aqueous sodium hydroxide (55g in 100 mL of water). The resulting suspension was filtered. The filter cake was rinsed with water and suction dried to afford 9.9 g (97%) of A1.5 as a PiPLC: 99%, ret. time = 0.92 min., LC/MS (M+H)+ = 202.06 (204.04, 206.02).
75%
A1.5: 4,6-Dichloro-l -methyl- lH-imidazo[4,5-c1pyridine A1.5A solution of sodium nitrite (415 mg; 6 mmol) in 2 ml of water was added drop wise over 5 minutes to a stirred solution of A1.4 (0.87 g; 4 mmol) in 14 ml of 50% aqueous H3PO2 at 0 C. The reaction mixture was allowed to warm to room temperature over ~2hr. After diluting the reaction mixture with water (250 ml) and re-cooling to 0 C, the ph was adjusted to ~9 by carefully adding solid sodium carbonate. The resulting suspension was filtered. The filter cake was rinsed with water and suction dried to afford 061 g (75%) of A1.5 as a HPLC: 99%, ret. time = 0.92 min., LC/MS (M+H)+ = 202.05 (204.04, 206.02).
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