Methanol → HCID 10385316, compound

HRID 747126Notes

Reaction equation

HRID 747126 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[NH:15][C:16]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[N:19]=[CH:18][N:17]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].CO.CCOC(C)=O>C1COCC1>[F:31][C:28]([F:29])([F:30])[C:25]1[CH:26]=[CH:27][C:22]([C:20]2[N:19]=[CH:18][N:17]=[C:16]([NH:15][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[C:8]=3[NH:7][C:6]([CH2:4][OH:3])=[CH:14]4)[CH:21]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 23577232HCID 23577232, compound

Product 1

HCID 10385316HCID 10385316, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 7-[6-(4-trifluoromethylphenyl)pyrimidin-4-ylamino]-1H-indole-2-carboxylic acid ethyl ester (285 mg, 0.67 mmol) in THF (2 mL) at 0° C. was added 1 M solution of LiAlH4 in THF (1.0 mL, Aldrich). The mixture was stirred at room temperature and the progress of the reaction was monitored by thin-layer chromatography. After completion of the reaction, to the mixture was added Na2SO4.10H2O (2 g), followed by the addition of MeOH (1 mL) and EtOAc (20 mL) with stirring at 0° C. The stirring was continued for 5 min and the mixture was filtered through a pad of Celite®. The filtrate was concentrated under vacuo and the residue was purified by silica gel column chromatography with gradient from 2% to 10% solution of (2 M NH3 in MeOH) in CH2Cl2 to afford the title compound as a yellow solid. MS (ESI, pos. ion.) m/z: 385 (M+1). MP: 221-223° C.

Workup

  1. customAfter completion of the reaction
  2. stirringwith stirring at 0° C
  3. filtrationthe mixture was filtered through a pad of Celite®
  4. concentrationThe filtrate was concentrated under vacuo
  5. customthe residue was purified by silica gel column chromatography with gradient from 2% to 10% solution of (2 M NH3 in MeOH) in CH2Cl2

Sources & evidence

ORD record
ord-16d59a87ce3f4a1abccf4d904072c0b8
Source dataset
uspto-grants-2008_07
Patent number
US07396831B2

Reaction notes

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