2-(6-bromopyridin-2-yl)ethanol

Step GA solution of LDA was prepared by adding a 1.6 M solution of n-butyllithium in hexane (51 mL, 81.2 mmol) at 0° C. to a stirred solution of N, N'-diisopropylamine (13.5 mL, 97.4 mmol) in tetrahydrofuran (60 mL). The mixture was stirred at 0° C. for 15 min and then added at -78° C. to a solution of commercially available 2-bromo-6-methyl-pyridine (5 g, 29.1 mmol) in tetrahydrofuran (90 mL). The mixture was stirred at -78° C. for 25 minutes and then N, N'-dimethylformamide (7.9 mL, 107 mmol) was added. After 30 minutes at -78° C., methanol (80 mL) and acetic acid (6.1 mL, 132 mmol) were added. Then sodium borohydride (1.1 g, 28 mmol) was added at -78° C. and the mixture was stirred overnight and allowed to reach room temperature. The reaction mixture was diluted with ethylacetate (150 mL) and washed with a 10percent citric acid solution (80 mL) and brine (80 mL). The organic phase was separated and the aqueous phase extracted with ethylacetate (2.x.150 mL). The combined organic phase was dried over NaStep G; A solution of LDA was prepared by adding a 1.6 M solution of n-butyllithium in hexane (51 mL, 81.2 mmol) at 0 °C to a stirred solution of N, N'-diisopropylamine (13.5 mL, 97.4 mmol) in tetrahydrofuran (60 mL). The mixture was stirred at 0 °C for 15 min and then added at -78 °C to a solution of commercially available 2-bromo-6-methyl-pyridine (5 g, 29.1 mmol) in tetrahydrofuran (90 mL). The mixture was stirred at -78 °C for 25 minutes and then N, N'-dimethylformamide (7.9 mL, 107 mmol) was added. After 30 minutes at -78 °C, methanol (80 mL) and acetic acid (6.1 mL, 132 mmol) were added. Then sodium borohydride (1.1 g, 28 mmol) was added at -78 °C and the mixture was stirred overnight and allowed to reach room temperature. The reaction mixture was diluted with ethylacetate (150 mL) and washed with a 10 percent citric acid solution (80 mL) and brine (80 mL). The organic phase was separated and the aqueous phase extracted with ethylacetate (2 x 150 mL). The combined organic phase was dried over NaA solution of LDA was prepared by adding a 1.6 M solution of n-butyllithium in hexane (51 mL, 81.2 mmol) at 0 °C to a stirred solution of N, N'-diisopropylamine (13.5 mL, 97.4 mmol) in tetrahydrofuran (60 mL). The mixture was stirred at 0 °C for 15 min and then added at -78 °C to a solution of commercially available 2-bromo-6-methyl-pyridine (5 g, 29.1 mmol) in tetrahydrofuran (90 mL). The mixture was stirred at -78 °C for 25 minutes and then Ν, Ν'- dimethylformamide (7.9 mL, 107 mmol) was added. After 30 minutes at -78 °C, methanol (80 mL) and acetic acid (6.1 mL, 132 mmol) were added. Then sodium borohydride ( 1.1 g, 28 mmol) was added at -78 °C and the mixture was stirred overnight and allowed to reach room temperature. The reaction mixture was diluted with ethylacetate (150 mL) and washed with a 10 percent citric acid solution (80 mL) and brine (80 mL). The organic phase was separated and the aqueous phase extracted with ethylacetate (2 x 150 mL). The combined organic phase was dried over NaTo a stirred solution of n-butyllithium (1 L, 1 .6 M in hexane) in tetrahydrofuran was added diisopropylamine (600 mL) dropwise through a dropping funnel at -10 °C under an NTo a stirred solution of n-butyllithium (1 L, 1 .6 M in hexane) in tetrahydrofuran was added diisopropylamine (600 mL) dropwise through a dropping funnel at -10 °C under an NPreparative Example 65 (0977) (0978) Step A (0979) To a stirred solution of n-butyllithium (1 L, 1.6 M in hexane) in tetrahydrofuran was added diisopropylamine (600 mL) dropwise through a dropping funnel at −10° C. under an N

Used in the preparation of 2,6-diaminopyridine compounds for treating diseases associated with amyloid or amyloid-like proteins, especially ocular diseases.

Molecular Weight:202.05
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:200.97893
Monoisotopic Mass:200.97893
Topological Polar Surface Area:33.1
Heavy Atom Count:10
Complexity:99.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes