Methanol → HCID 58094830, compound

HRID 2282137Notes

Reaction equation

HRID 2282137 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:23]#[N:24])=[C:11]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([F:22])[CH:17]=2)[S:12][C:13]=1[CH:14]=O.CO.[C:27](=O)([O-])[O-].[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:23]#[N:24])=[C:11]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([F:22])[CH:17]=2)[S:12][C:13]=1[C:14]#[CH:27]

Participants

5

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 58094746HCID 58094746, compoundHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 58094830HCID 58094830, compound

Procedure

To a stirred solution of 4-(2,4-dichlorophenyl)-2-(2-fluoropyridin-4-yl)-5-formylthiophene-3-carbonitrile (200.0 mg, 0.5302 mmol) in dry MeOH (12 mL, 3.0E2 mmol) was added Potassium carbonate (161 mg, 1.17 mmol) and dimethyl 1-diazo-2-oxopropylphosphonate (132 mg, 0.689 mmol). The mixture was stirred at rt for 2 h. The mixture was quenched by sodium bicarbonate solution and extracted with EtOAc. The organic layer was dried and evaporated. The residue was purified by column chromatography to afford the title compound. LC/MS (A) ES+ 373, 375. 1H NMR (400 MHz, d1-chloroform) δ: 8.39 (1H, d, J=5.29 Hz), 7.61 (2H, ddd, J=6.19, 3.83, 1.68 Hz), 7.45-7.31 (3H, m), 3.49 (1H, s)

Workup

  1. customThe mixture was quenched by sodium bicarbonate solution
  2. extractionextracted with EtOAc
  3. customThe organic layer was dried
  4. customevaporated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-21168b339376430caffe82774f698242
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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