Reacción #1100486

Ecuación de reacción

solution

methyl 3-formyl-1-(3-(naphthalen-1-yloxy)propyl)-4-o-tolyl-1H-indole-2-carboxylate

sodium triacetoxyborohydride

morpholine

→

4-(2-methylphenyl)-3-(morpholin-4-ylmethyl)-1-(3-(1-naphthyloxy)propyl)-1H-indole-2-carboxylic acid

Disolventes

dichloroethane

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with water, brine
2. 2
   Secadodried over Na2SO4
3. 3
   workup.DISSOLUTIONThe residue was dissolved in tetrahydrofuran (4 ml)
4. 4
   workup.ADDITIONmethanol (2 mL) and water (2 ml) and LiOH (100 mg) was added
5. 5
   workup.STIRRINGThe mixture was stirred at room temperature overnight
6. 6
   ConcentraciónThe mixture was concentrated
7. 7
   Extracciónextracted with ethyl acetate (100 mL×3)
8. 8
   OtroThe combined extracts were dried
9. 9
   Concentraciónconcentrated
10. 10
    Otroto give crude product, which
11. 11
    Otrowas purified by RPHPLC

Procedimiento

To a solution of EXAMPLE 107C (50 mg) in dichloroethane (3 ml) was added sodium triacetoxyborohydride (35 mg) and morpholine (15 mg). The mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate (200 ml) and washed with water, brine, and dried over Na2SO4. The residue was dissolved in tetrahydrofuran (4 ml), methanol (2 mL) and water (2 ml) and LiOH (100 mg) was added. The mixture was stirred at room temperature overnight. The mixture was concentrated and the residue neutralized with aqueous NH4Cl and extracted with ethyl acetate (100 mL×3). The combined extracts were dried and concentrated to give crude product, which was purified by RPHPLC. 1H NMR (300 MHz, dimethyl sulfoxide-d6) δ 8.25 (m, 1H), 7.86 (m, 2H), 7.45 (m, 9H), 6.93 (m, 2H), 4.99 (m, 2H), 4.47 (m, 1H), 4.25 (t, 2H), 3.60 (m, 10H), 2.43 (m, 2H), 1.92 (s, 3H).

Fuente