Potassium Carbonate → HCID 59359757, compound

HRID 1187274Notes

Reaction equation

HRID 1187274 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[O:12][CH:13]([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].[S:22]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23]1>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:13]([O:12][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:24]3[CH:25]=[CH:26][S:22][CH:23]=3)[CH:3]=2)[N:8]=[CH:7][N:6]=1)([CH3:15])[CH3:14]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 581760Thiophene-3-boronic acidHCID 59359758HCID 59359758, compound

Product 1

HCID 59359757HCID 59359757, compoundYield 55.2%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 6-bromo-4-isopropoxy-quinazoline (17.9 mg, 0.067 mmol), potassium carbonate (0.13 mmol), tetrakis(triphenylphosphine) palladium (10 mg) and 3-thiophenyl boronic acid (0.08 mmol) in DME (1 ml) and water (0.5 ml) was heated to 50° C. for 30 minutes. The reaction mixture was filtered through a 0.45 micron filter and diluted with ethyl acetate (2 ml). The organic layer was washed with water (1 ml), separated, and concentrated in vacuo. The residue was purified by passage through a pre-packed silica gel column, eluting with ethyl acetate. The solvents were concentrated in vacuo to provide the desired product as a white solid (10 mg, yield: 55%). The resulting compound was characterized as follows: MS (m/z) 271.09 [M+H]+; HPLC Rt=1.83 minutes (Method A).

Workup

  1. filtrationThe reaction mixture was filtered through a 0.45 micron
  2. filtrationfilter
  3. additiondiluted with ethyl acetate (2 ml)
  4. washThe organic layer was washed with water (1 ml)
  5. customseparated
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by passage through a pre-packed silica gel column
  8. washeluting with ethyl acetate
  9. concentrationThe solvents were concentrated in vacuo

Sources & evidence

ORD record
ord-76c173a166074b449f9d39513e5a4d19
Source dataset
uspto-grants-2014_03
Patent number
US08673929B2

Reaction notes

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