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

HRID 1156582Notes

Reaction equation

HRID 1156582 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. additionTo a suspension of 9.9 g
  2. additionAfter addition
  3. temperaturethen cooled to 0°
  4. customquenched by the addition dropwise of 20 ml
  5. filtrationThe resulting solids are filtered
  6. dry with materialthe tetrahydrofuran dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-f28306ce15254d3b99f73e06bc783c5b
Source dataset
uspto-grants-1982_06
Patent number
US04336379

Reaction notes

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