Ethyl Acetate → HCID 86728244, compound

HRID 1776839Notes

Reaction equation

HRID 1776839 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:19][CH2:18][N:8]3[C:9]4[CH:10]=[CH:11][CH:12]=[C:13]([C:16]#N)[C:14]=4[CH:15]=[C:7]3[C:6]=2[N:20]=1.CC(C[AlH]CC(C)C)C.CC[O:32]C(C)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:19][CH2:18][N:8]3[C:9]4[CH:10]=[CH:11][CH:12]=[C:13]([CH:16]=[O:32])[C:14]=4[CH:15]=[C:7]3[C:6]=2[N:20]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 86728245HCID 86728245, compound

Product 1

HCID 86728244HCID 86728244, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-chloro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole-11-carbonitrile (500 mg, 1.77 mmol) in toluene (10 mL) was added DIBAL-H (505 mg, 3.55 mmol) in portion under nitrogen at −78° C. and then the mixture was stirred at −78° C. for 6 hours. The reaction mixture was quenched with ice water and extracted with EtOAc. Then the combined organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo to provide the 2-chloro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indole-11-carbaldehyde (200 mg, yield: 40%) through the column chromatography (petroleum ether:EtOAc=5:1˜2:1). 1H-NMR (CDCl3, 400 MHz) δ 10.29 (s, 1H), 8.03 (s, 1H), 7.69 (dd, J1=0.8 Hz, J2=7.2 Hz, 1H), 7.56 (d, J=8.4 Hz, 1H), 7.44 (t, J=8.0 Hz, 1H), 7.38 (d, J=8.4 Hz, 1H), 7.22 (d, J=8.4 Hz, 1H), 6.05 (s, 2H). MS (M+H)+: 285/287.

Workup

  1. customThe reaction mixture was quenched with ice water
  2. extractionextracted with EtOAc
  3. washThen the combined organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2befad6c689342029bc462e15dfa2429
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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