Water → HCID 69382578, compound

HRID 1351748Notes

Reaction equation

HRID 1351748 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[C:19]([CH3:20])=[C:18]2[C:14]([C:15]3[CH2:24][CH2:23][O:22][C:21]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])([CH2:25][CH2:26][CH3:27])[C:16]=3[NH:17]2)=[C:13](Br)[CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:35][N:36]1C(=O)CCC1.C([Cu])#N.O>CCOC(C)=O>[CH2:1]([O:8][C:9]([C:11]1[C:19]([CH3:20])=[C:18]2[C:14]([C:15]3[CH2:24][CH2:23][O:22][C:21]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])([CH2:25][CH2:26][CH3:27])[C:16]=3[NH:17]2)=[C:13]([C:35]#[N:36])[CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 69383342HCID 69383342, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 69382578HCID 69382578, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
190 °C

Procedure

A 500 mL RBF was charged with 5-bromo-1-ethoxycarbonylmethyl-8-methyl-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indole-7-carboxylic acid benzyl ester (12.00 g, 23 mmol), NMP (100 mL), and CuCN (20.34 g, 0.227 mol). The reaction was heated to 190° C. with vigorous stirring for 45 minutes. The reaction was then cooled to ambient temperature, diluted with EtOAc followed by water (300 mL). A 1:1 mixture of Celite/silica gel were added to the mixture. This suspension was stirred for several minutes and filtered through a pad of Celite. The Celite pad was washed with EtOAc, and the filtrate was washed with water (5×) and saturated NaCl (1×), dried over MgSO4, and concentrated. Upon trituration with hexanes, 8.82 g (81.8%) of a light tan solid was obtained. 1H NMR (CDCl3) δ 10.11 (br s, 1H), 8.12 (s, 1H), 7.40 (m, 5H), 5.37 (s, 2H), 4.22 (m, 2H), 3.95 (m, 2H), 3.00 (m, 4H), 2.83 (s, 3H), 2.00 (m, 2H), 1.30 (m, 5H), 0.89 (t, J=7.6 Hz, 3H).

Workup

  1. temperatureThe reaction was then cooled to ambient temperature
  2. additionA 1:1 mixture of Celite/silica gel
  3. additionwere added to the mixture
  4. stirringThis suspension was stirred for several minutes
  5. filtrationfiltered through a pad of Celite
  6. washThe Celite pad was washed with EtOAc
  7. washthe filtrate was washed with water (5×) and saturated NaCl (1×)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b94e450b75b0435c997014186c9e840c
Source dataset
uspto-grants-2007_05
Patent number
US07217730B2

Reaction notes

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