Benzoic acid, 2-iodo-, methyl ester → HCID 118131433, compound

HRID 634347Notes

Reaction equation

HRID 634347 reaction equation
I[C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:12][CH:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:14]#[CH:15]>CN(C=O)C.CCN(CC)CC.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.[Cu]I>[C:19]([O:18][C:17]([NH:16][CH:13]([CH3:12])[C:14]#[C:15][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[O:23])([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 2

HCID 69132Benzoic acid, 2-iodo-, methyl esterHCID 10725814tert-Butyl but-3-yn-2-ylcarbamate2×

Product 1

HCID 118131433HCID 118131433, compoundYield 51.2%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

Pd(Ph3P)4 (683 mg, 0.591 mmol), CuI (938 mg, 49.2 mmol), methyl 2-iodobenzoate (25.8 g, 98.49 mmol), tert-butyl but-3-yn-2-ylcarbamate (intermediate 3.2, 25 g, 147.75 mmol) in DMF (30 ml) and Et3N (27 ml) were mixed in DMF (125 ml) and the mixture was heated to 60° C. under nitrogen atmosphere for 12 hrs. The mixture was quenched with water and the product extracted with EtOAc. The collected organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. The residual was purified by column chromatography over silica gel (Hex/EtOAc 9:1) to give the title compound (15.3 g, 51%).

Workup

  1. customThe mixture was quenched with water
  2. extractionthe product extracted with EtOAc
  3. dry with materialThe collected organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residual was purified by column chromatography over silica gel (Hex/EtOAc 9:1)

Sources & evidence

ORD record
ord-c0e3f6e680854a50ad9a1dc0e8227870
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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