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ChemicalBook CAS DataBase List CHEMBRDG-BB 4010855
894852-67-6

CHEMBRDG-BB 4010855 synthesis

2synthesis methods
-

Yield:894852-67-6 71%

Reaction Conditions:

Stage #1: 2-formyl-3-methylindole;methylamine in methanol;ethanol; for 5 h;
Stage #2: with sodium tetrahydroborate in methanol;ethanol at 0 - 20;
Stage #3: with water in methanol;ethanol at 0;

Steps:

60.a

a) Preparation of 3-methyl-2-(methylaminomethyl)indole; Methylamine (0.34 niL, 8.4 mmol, 33% in ethanol) was added to a solution of 3- methylindole-2-carboxaldehyde (447 mg, 2.8 mmol) in methanol (10 mL) and stirred for 5 hours. Sodium borohydride (104 mg, 2.8 mmol) was slowly added at 00C. The resultant mixture was warmed to room temperature and stirred overnight. Water (2 mL) was added slowly at 0 0C and the mixture was evaporated to a paste. The paste was partitioned between water (2 niL) and dichloromethane (15 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (2 x 15 mL). The combined organic phases were dried and evaporated to afford title compound (348 mg, 71%). 1H NMR (400 MHz, DMSO-de): 10.63 (s, IH), 7.38 (d, J = 7.7 Hz, IH), 7.25 (d, J = 8.0 Hz, IH), 6.99 (t, J - 8.0 Hz, IH), 6.92 (t, J = 6.6 Hz, IH), 3.73 (s, 2H), 2.25 (s, 3H), 2.19 (s, 3H)

References:

WO2007/53131,2007,A2 Location in patent:Page/Page column 166-167

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