Tetrahydrofuran → HCID 59454958, compound

HRID 1401632Notes

Reaction equation

HRID 1401632 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[C:9]2[C:10]3([CH2:19][CH:20](C(C)(C)C(=O)C4C=CN=CC=4)[NH:21][CH:22]=2)[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]([CH:17]=O)C3.[CH2:34]1[CH2:38][O:37][CH2:36][CH2:35]1>>[CH3:36][O:37]/[C:38](/[C:34]1[CH:35]=[CH:14][N:13]=[CH:12][CH:17]=1)=[C:12](\[N:13]1[C:14]2[CH:15]=[CH:16][C:8]([CH3:7])=[CH:9][C:10]=2[C:19]2[CH2:20][N:21]([CH3:22])[CH2:16][CH2:8][C:7]1=2)/[CH3:17]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 86644769HCID 86644769, 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-d]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-1eb7bfa5c55b474ca22fe6616dc0ddea
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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