Dimethyl dicarbonate → HCID 67110182, compound

HRID 2381240Notes

Reaction equation

HRID 2381240 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([O:20][CH3:21])=[CH:11][C:12]([C:18]#[N:19])=[C:13]([CH:17]=1)[C:14]([OH:16])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O.COC(OC(OC)=O)=O.[O-][Si]([O-])=O.[Mg+2]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.O1CCOCC1>[CH2:1]([O:8][C:9]1[C:10]([O:20][CH3:21])=[CH:11][C:12]([C:18]#[N:19])=[C:13]([C:14](=[O:16])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[F:22])[CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 3086Dimethyl dicarbonateHCID 61680MAGNESIUM SILICATE (synthetic)HCID 27343542-Fluorophenylboronic acidHCID 583455292-Cyano-4-methoxy-5-(phenylmethoxy)benzoic acid

Product 1

HCID 67110182HCID 67110182, compoundYield 52.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-benzyloxy-2-cyano-4-methoxybenzoic acid (reference example 5-3) (502 mg), 2-fluorophenylboronic acid (297 mg), tetrakis(triphenylphosphine)palladium(0) (205 mg), dimethylpyrocarbonate (2 mL) and 1,4-dioxane (10 mL) was stirred at 80° C. under an argon atmosphere for 1.25 hours. Ethyl acetate and Florisil (registered mark) (2 g) were added. After stirring for 15 minutes, the mixture was passed through a layer of Celite (registered mark). The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 5%-30% ethyl acetate/hexane, gradient elution) to give the title compound (338 mg).

Workup

  1. stirringAfter stirring for 15 minutes
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent: 5%-30% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record
ord-c2785e5f1ecf4147832a981f62a33ac5
Source dataset
uspto-grants-2012_09
Patent number
US08258162B2

Reaction notes

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