Dimethylformamide → HCID 21866786, compound

HRID 857224Notes

Reaction equation

HRID 857224 reaction equation
CN(C)[CH:3]=[O:4].Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][C:14]2[N:15]=[C:16]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)[O:17][C:18]=2[CH3:19])[CH:8]=1.C([O-])=O.[Na+]>C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:19][C:18]1[O:17][C:16]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)=[N:15][C:14]=1[CH2:13][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[CH:3]=[O:4]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 2723810Sodium FormateHCID 21866606HCID 21866606, compound

Product 1

HCID 21866786HCID 21866786, compound

Reagents, catalysts & solvents 2

HCID 178419050HCID 178419050, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

N,N-Dimethylformamide (30 ml) was added to 9.48 g of 1-bromo-3-{[5-methyl-2-(p-tolyl)oxazol-4-yl]methyl}benzene, 2.83 g of sodium formate and 0.97 g of bis(triphenylphosphine)palladium (II) dichloride, and the mixture was stirred for 9 hours at 110° C. under bubbling carbon monoxide. To the reaction solution was added water, and extracted with ethyl acetate, filtered to remove insolubles, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=4:1) to provide 3.58 g of the objective compound as colorless crystals. M.p. 98-99° C.

Workup

  1. extractionextracted with ethyl acetate
  2. filtrationfiltered
  3. customto remove insolubles
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=4:1)

Sources & evidence

ORD record
ord-4d44b80c585b4b7e99202797c666ae12
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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