Dichloromethane → HCID 10421666, compound

HRID 1376136Notes

Reaction equation

HRID 1376136 reaction equation
CON(C)[C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[NH:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-].ClCCl>C1COCC1>[N:19]1[CH:18]=[CH:17][C:16]([NH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:4]=[O:5])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 86590774HCID 86590774, compound

Product 1

HCID 10421666HCID 10421666, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

At 0° C. stir a suspension of 3-(pyridin-4-ylamino)-1H-indole-2-carboxylic acid methoxy-methyl-amide (2.72 g, 7.2 mmol) in THF (35 mL), and add a 1M solution of LAH in THF (14.5 mL, 14.5 mmol). Allow warming to room temperature and continue to stir for 20 h. Add aqueous NH4Cl followed by dichloromethane. Filter the aluminum salts, separate the organic phase and concentrate it under vacuum to obtain a brown oil. Flash chromatograph the oil to obtain 0.62 g (36%) of the title compound as a yellow solid. 1H NMR (DMSO-d6) δ 11.8 (1H, s), 9.95 (1H, s), 9.1 (1H, s), 8.18 (2H, brs), 7.4 (3H, m), 7.1 (1H, dd), 6.7 (2H, brd).

Workup

  1. temperatureAllow warming to room temperature
  2. stirringto stir for 20 h
  3. filtrationFilter the aluminum salts
  4. customseparate the organic phase
  5. concentrationconcentrate it under vacuum
  6. customto obtain a brown oil

Sources & evidence

ORD record
ord-a01fffa5984d43ae995c34c3e730baaf
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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