Diethyl (cyanomethyl)phosphonate → HCID 70562878, compound

HRID 1427241Notes

Reaction equation

HRID 1427241 reaction equation
[C:1](CP(=O)(OCC)OCC)#[N:2].[Li+].[Cl-].[CH2:14]1CCN2C(=NCCC2)CC1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([N:37]2[C:45]3[C:40](=[C:41]([NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[CH:42]=[CH:43][CH:44]=3)[CH:39]=[CH:38]2)([CH2:35][CH3:36])[CH:33]=O)=[CH:28][CH:27]=1>C(#N)C>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]([N:37]2[C:45]3[C:40](=[C:41]([NH:46][C:47](=[O:53])[O:48][C:49]([CH3:51])([CH3:52])[CH3:50])[CH:42]=[CH:43][CH:44]=3)[CH:39]=[CH:38]2)([CH2:33][CH3:14])/[CH:35]=[CH:36]/[C:1]#[N:2])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 433294Lithium ChlorideHCID 86705043HCID 86705043, compound

Product 1

HCID 70562878HCID 70562878, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a mixture of diethyl cyanomethylphosphonate (145 mg, 0.76 mmol), LiCl (43 mg, 1.01 mmol) and DBU (255 mg, 1.01 mmol) in acetonitrile (15 mL) was added a solution of tert-butyl 1-(2-(4-chlorophenyl)-1-oxobutan-2-yl)-1H-indol-4-ylcarbamate (210 mg, 1.02 mmol), as described in Example 21 Step B, in acetonitrile (3 mL). The mixture was stirred at room temperature for 2 h and the volatile was evaporated. The residue was purified by silica gel chromatography eluting with PE/EA (10/1 to 3/1, v/v) to afford the title compound as a white solid. LC/MS m/z=458.1 [M+Na]+.

Workup

  1. customthe volatile was evaporated
  2. customThe residue was purified by silica gel chromatography
  3. washeluting with PE/EA (10/1 to 3/1

Sources & evidence

ORD record
ord-bf8d14f42120495ca623b6856bc18ede
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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