1,2-Dimethoxyethane → HCID 57662937, compound

HRID 406826Notes

Reaction equation

HRID 406826 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH:13]1[C:21]2[C:16](=[CH:17][C:18](B(O)O)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1.C(N(CC)CC)C.C(COC)OC>C(OCC)(=O)C.O>[Cl:1][C:2]1[N:11]=[C:10]([C:18]2[CH:17]=[C:16]3[C:21](=[CH:20][CH:19]=2)[NH:13][CH:14]=[CH:15]3)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 8471TriethylamineHCID 2528862,4-DichloroquinazolineHCID 27343615-Indolylboronic acid

Product 1

HCID 57662937HCID 57662937, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a round bottomed flask containing 2,4-dichloroquinazoline (800 mg, 4.02 mmol) was added indol-5-boronic acid (647 mg, 4.02 mmol), dichloro-((bis-diphenylphosphino)-ferrocenyl)-palladium (II) (complex with methylene chloride, 235 mg, 0.32 mmol), triethylamine (1.5 mL, 10 mmol), dimethoxyethane (20 mL), and water (0.5 mL). The reaction mixture was heated at 80° C. for 14 h, then cooled to rt and diluted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, dried over sodium sulfate, filtered, and concentrated on a rotary evaporator. The material was purified by flash column chromatography to afford 2-chloro-4-(1H-indol-5-yl)quinazoline as a brown solid (740 mg, 66%).

Workup

  1. temperaturecooled to rt
  2. washThe organic layer was washed with saturated sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator
  6. customThe material was purified by flash column chromatography

Sources & evidence

ORD record
ord-6c388db2e9c44d3296168e18a9513045
Source dataset
uspto-grants-2014_06
Patent number
US08754092B2

Reaction notes

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