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Dimethylformamide → (5-Chloro-6-phenylethynyl-1H-benzoimidazol-2-ylsulfanylmethyl)-phosphonic acid diethyl ester

HRID 2193852
Notes
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Reaction equation

HRID 2193852 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][S:10][C:11]1[NH:15][C:14]2[CH:16]=[C:17]([Cl:21])[C:18](I)=[CH:19][C:13]=2[N:12]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[C:22]1([C:28]#[CH:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN(CC)CC.CN(C=O)C>CCOC(C)=O.[Cu]I>[CH2:1]([O:3][P:4]([CH2:9][S:10][C:11]1[NH:12][C:13]2[CH:19]=[C:18]([C:29]#[C:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:17]([Cl:21])=[CH:16][C:14]=2[N:15]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 58422987(6-Chloro-5-iodo-1H-benzoimidazol-2-ylsulfanylmethyl)-phosphonic acid diethyl ester2×

Product 1

HCID 58422995(5-Chloro-6-phenylethynyl-1H-benzoimidazol-2-ylsulfanylmethyl)-phosphonic acid diethyl ester

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (6-Chloro-5-iodo-1H-benzoimidazol-2-ylsulfanylmethyl)-phosphonic acid diethyl ester (Intermediate 1, 0.4 g, 1.0 mmol), phenyl acetylene (0.26 mL, 2.0 mmol), PdCl(PPh3)2 (0.34 g, 0.050 mmol), CuI (0.018 g, 0.1 mmol), Et3N (0.96 mL, 6.94 mmol), and 10.0 mL of DMF was heated to 120° C. for 10 minutes using a microwave reactor. HPLC indicated the reaction was complete. The crude mixture was diluted with 40 mL EtOAc and washed with 3×40 mL H2O. The organic fractions were separated, combined, dried over MgSO4, and concentrated in vacuo to afford an oil. This oil was purified by MPLC to afford title compound 1-1 as clear oil.

Workup

  1. washwashed with 3×40 mL H2O
  2. customThe organic fractions were separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto afford an oil
  6. customThis oil was purified by MPLC

Sources & evidence

ORD record
ord-fffab433764244fda1c96a2cb2a9e472
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08329914B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes