Triethylamine → HCID 86630914, compound

HRID 220111Notes

Reaction equation

HRID 220111 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22](I)[CH:23]=3)[N:18]=[CH:17][N:16]=2)=[CH:10][CH:9]=1.[CH:29]([O-])=[O:30].[Na+].C(N(CC)CC)C>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([CH:29]=[O:30])[CH:23]=3)[N:18]=[CH:17][N:16]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2723810Sodium FormateHCID 68751757HCID 68751757, compound

Product 1

HCID 86630914HCID 86630914, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In 100 ml of dimethylformamide was dissolved 4-(4-(3-fluorobenzyloxy)phenylamino)-6-iodoquinazoline hydrochloride (III-1, 5.0 g), and 1.25 g of sodium formate, dichlorobis(triphenylphosphine)palladium (324 mg), and triethylamine (3.2 ml) were added. The reaction mixture was degassed, and stirred under heating at 80° C. for 3 hours under the carbon monoxide atmosphere. Thereafter, the reaction mixture was poured into ice water, and extracted with ethyl acetate. The extract was washed with water and sodium chloride solution, and dried with magnesium sulfate. The dried solution was filtered with Celite, concentrated, and powdered with an ethyl acetate-hexane (1:2) to obtain 4-(4-(3-fluorobenzyloxy)phenylamino)-6-formylquinazoline (IV-1, 2.86 g) as a yellow solid.

Workup

  1. additionwere added
  2. customThe reaction mixture was degassed
  3. additionThereafter, the reaction mixture was poured into ice water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water and sodium chloride solution
  6. dry with materialdried with magnesium sulfate
  7. filtrationThe dried solution was filtered with Celite
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f92876682475495db44cecbb93d41a0a
Source dataset
uspto-grants-2012_06
Patent number
US08202879B2

Reaction notes

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