HCID 1600806, compound → 2-(Dimethylamino)-1-[2-(3-ethyl-5-methyl-1,2-oxazol-4-yl)-1H-indol-3-yl]ethan-1-ol

HRID 615449Notes

Reaction equation

HRID 615449 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH3:30])[C:9](=O)[C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][C:13]=1[C:21]1[C:22]([CH2:27][CH3:28])=[N:23][O:24][C:25]=1[CH3:26])=[O:11]>O1CCCC1>[CH3:30][N:8]([CH2:9][CH:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][C:13]=1[C:21]1[C:22]([CH2:27][CH3:28])=[N:23][O:24][C:25]=1[CH3:26])[OH:11])[CH3:7]

Participants

4

Reactant 2

HCID 1600806HCID 1600806, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 1332982-(Dimethylamino)-1-[2-(3-ethyl-5-methyl-1,2-oxazol-4-yl)-1H-indol-3-yl]ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 9.9 g (0.26 mole) of lithium aluminum hydride and 950 ml. tetrahydrofuran under nitrogen there is added 21.0 g. (0.065 mole) of N,N-dimethyl-2-(3-ethyl-5-methyl-4-isoxazolyl)-3-indoleglyoxylamide in 735 ml. of tetrahydrofuran, while maintaining the temperature between 20° to 25° C. After addition is complete, the mixture is stirred at room temperature for 5 hours then cooled to 0° and quenched by the addition dropwise of 20 ml. of water in 180 ml. of tetrahydrofuran. The resulting solids are filtered and the tetrahydrofuran dried over anhydrous magnesium sulfate, filtered and evaporated. The residue is recrystallized from ethanol to give α-(dimethylaminomethyl)-2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indole-3-methanol; m.p. 178° to 180° C.

Workup

  1. additionAfter addition
  2. temperaturethen cooled to 0°
  3. customquenched by the addition dropwise of 20 ml
  4. filtrationThe resulting solids are filtered
  5. dry with materialthe tetrahydrofuran dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-e12e68a150f34dd2be05974c51e3968c
Source dataset
uspto-grants-1985_02
Patent number
US04499279

Reaction notes

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