Ammonium Hydroxide → HCID 68701783, compound

HRID 2235097Notes

Reaction equation

HRID 2235097 reaction equation
C([BH3-])#N.[Na+].[CH3:5][O:6][C:7]([C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[C:11]([O:18][CH3:19])[CH:10]=1)=[O:8].[OH-].[NH4+]>C(O)(=O)C.O>[CH3:5][O:6][C:7]([C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14][NH:15]2)=[C:11]([O:18][CH3:19])[CH:10]=1)=[O:8]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 12140116Methyl 4-methoxy-1H-indole-6-carboxylate

Product 1

HCID 68701783HCID 68701783, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Sodium cyanoborohydride (3.6 g, 57.8 mmol, 3 equiv.) was added to a stirred solution of 4-methoxy-1H-indole-6-carboxylic acid methyl ester (3.96 g, 19.3 mmol, 1 equiv.) in acetic acid (40 mL) at room temperature over 5 minutes. The mixture was stirred for 30 minutes, then cooled to 0° C. and slowly poured onto concentrated ammonium hydroxide (78 mL, d=0.880) at 0° C. The mixture was diluted with water (20 mL) extracted with dichloromethane (4×25 mL). The organic layers were combined, dried over Na2SO4 and the solvent was removed under vacuum. The crude mixture was purified by flash column chromatography (SiO2, dichloromethane) and the fractions combined to afford 4-methoxy-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester, 2.8 g (70% yield). LC @215 nm; Rt 0.85: 97%, m/z (ES+): 208 (M+H+.); δH (400 MHz; d6-DMSO) 6.90 (1H, s), 6.86 (1H, s), 3.80 (3H, s), 3.79 (3H, s), 3.49 (2H, t), 2.89 (2H, t).

Workup

  1. extractionextracted with dichloromethane (4×25 mL)
  2. dry with materialdried over Na2SO4
  3. customthe solvent was removed under vacuum
  4. customThe crude mixture was purified by flash column chromatography (SiO2, dichloromethane)

Sources & evidence

ORD record
ord-da585ef13b844494bec938c68e75ebd3
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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