Tetrahydrofuran → HCID 59454958, compound

HRID 1400563Notes

Reaction equation

HRID 1400563 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[CH:16]=[CH:15][C:14]2[N:13]([C:17](C)([CH3:26])[C:18](=[O:25])[C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[C:12]3[CH2:28][CH2:29][N:30]([CH:32]=O)[CH2:31][C:11]=3[C:10]=2[CH:9]=1.[CH2:34]1COCC1>>[CH3:34][O:25]/[C:18](/[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)=[C:17](\[N:13]1[C:14]2[CH:15]=[CH:16][C:8]([CH3:7])=[CH:9][C:10]=2[C:11]2[CH2:31][N:30]([CH3:32])[CH2:29][CH2:28][C:12]1=2)/[CH3:26]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 86690954HCID 86690954, compound

Product 1

HCID 59454958HCID 59454958, compound

Procedure

LAH (87 mg, 52.63 mmol) was taken in dry THF (10 mL) under inert atmosphere stirred for 10 min, 8-methyl-5-(2-methyl-1-oxo-1-(pyridin-4-yl)propan-2-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carbaldehyde (0.33 g, 0.914 mmol) was added portionwise and stirred at RT for 1 h. The reaction was monitored by TLC. LAH was quenched with sat. sodium sulfate (aqueous) at 0° C., filtered the reaction mass. The filtrate was extracted with EtOAc, dried over anhydrous sodium sulfate and evaporated to dryness to afford 0.24 g of the title compound as a yellow sticky solid. 1H NMR (CDCl3, free base) δ (ppm): 8.36 (d, 2H), 7.20 (s, 1H), 7.10 (d, 1H), 7.0 (d, 1H), 6.78 (d, 2H), 3.78 (s, 2H), 3.60 (s, 3H), 2.82 (m, 1H), 2.74 (m, 1H), 2.60 (m, 1H), 2.50 (s, 3H), 2.42 (s, 3H), 2.30 (m, 1H), 2.19 (s, 3H).

Workup

  1. stirringstirred at RT for 1 h
  2. customLAH was quenched with sat. sodium sulfate (aqueous) at 0° C.
  3. filtrationfiltered the reaction mass
  4. extractionThe filtrate was extracted with EtOAc
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-c121df79184e4368aba7f98582c3222f
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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