4-Amino-5-methoxy-1-methylindole-2-carboxylic acid methyl ester → (4-Amino-5-methoxy-1-methyl-1H-indol-2-yl)methanol

HRID 430932Notes

Reaction equation

HRID 430932 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[N:12]([CH3:23])[C:13]2[C:18]([CH:19]=1)=[C:17]([NH2:20])[C:16]([O:21][CH3:22])=[CH:15][CH:14]=2)=O>C1COCC1>[NH2:20][C:17]1[C:16]([O:21][CH3:22])=[CH:15][CH:14]=[C:13]2[C:18]=1[CH:19]=[C:11]([CH2:9][OH:8])[N:12]2[CH3:23]

Participants

4

Reactant 2

HCID 206071674-Amino-5-methoxy-1-methylindole-2-carboxylic acid methyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 18762535(4-Amino-5-methoxy-1-methyl-1H-indol-2-yl)methanolYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (5.84 mL, 5.84 mmol, 1.0 M solution in Et2O) was added to a solution of 10 (595 mg, 2.59 mmol) in THF (12 mL) under argon. The reaction was then heated at reflux for 15 min, quenched by careful addition of H2O followed by 1 M NaOH, then extracted with CH2Cl2 (3×). The combined organic layers were dried over Na2SO4 and evaporated to afford 11 (490 mg, 94%) as a brown oil which was used without further purification; 1H NMR (CDCl3): δ 6.95 (1H, d), 6.71 (1H, d), 6.34 (1H, s), 4.77 (2H, s), 3.87 (3H, s), 3.74 (3H, s).

Workup

  1. temperatureThe reaction was then heated
  2. temperatureat reflux for 15 min
  3. customquenched by careful addition of H2O
  4. extractionextracted with CH2Cl2 (3×)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-b1a5d320e3484431b4b5c40adb3f0e6f
Source dataset
uspto-grants-2003_12
Patent number
US06656926B2

Reaction notes

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