Diethyl (cyanomethyl)phosphonate → (E)-N-(1-(3-(4-chlorophenyl)-1-cyanopent-1-en-3-yl)-1H-indazol-4-yl)-N-((2-(trimethylsilyl)ethoxy)methyl)methanesulfonamide

HRID 1427235Notes

Reaction equation

HRID 1427235 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[Li+].[Cl-].C1CCN2C(=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]([N:46]([CH2:51][O:52][CH2:53][CH2:54][Si:55]([CH3:58])([CH3:57])[CH3:56])[S:47]([CH3:50])(=[O:49])=[O:48])[CH:42]=[CH:43][CH:44]=3)[CH:39]=[N:38]2)([CH2:35][CH3:36])[CH:33]=O)=[CH:28][CH:27]=1>CC#N>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([N:37]2[C:45]3[C:40](=[C:41]([N:46]([CH2:51][O:52][CH2:53][CH2:54][Si:55]([CH3:58])([CH3:56])[CH3:57])[S:47]([CH3:50])(=[O:49])=[O:48])[CH:42]=[CH:43][CH:44]=3)[CH:39]=[N:38]2)([CH2:35][CH3:36])/[CH:33]=[CH:3]/[C:1]#[N:2])=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 433294Lithium ChlorideHCID 86705041N-(1-(2-(4-chlorophenyl)-1-oxobutan-2-yl)-1H-indazol-4-yl)-N-((2-(trimethylsilyl) ethoxy)methyl)methanesulfonamide

Product 1

HCID 86705042(E)-N-(1-(3-(4-chlorophenyl)-1-cyanopent-1-en-3-yl)-1H-indazol-4-yl)-N-((2-(trimethylsilyl)ethoxy)methyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a mixture of diethyl cyanomethylphosphonate (20 mg, 0.12 mmol), LiCl (5 mg, 0.12 mmol) and DBU (18 mg, 0.12 mmol) in MeCN (2 mL) was added a solution of N-(1-(2-(4-chlorophenyl)-1-oxobutan-2-yl)-1H-indazol-4-yl)-N-((2-(trimethylsilyl)ethoxy)methyl) methane sulfonamide (50 mg, 0.10 mmol) in MeCN (1 mL). The mixture was stirred at room temperature for 2 h and evaporated. The residue was purified by silica gel chromatography (PE/EA=6/1) to afford the title compound as a white solid. LC/MS m/z=545.2 [M+H]+.

Workup

  1. customevaporated
  2. customThe residue was purified by silica gel chromatography (PE/EA=6/1)

Sources & evidence

ORD record
ord-dda7a6de15eb47329e00a7b27f152115
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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