1,2-Dimethoxyethane → 7-Chloro-4-(4-fluoro-3,5-dimethylphenyl)quinazoline

HRID 1056445노트

반응식

HRID 1056445 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[F:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17](B2OC(C)(C)C(C)(C)O2)=[CH:16][C:15]=1[CH3:30].C(=O)([O-])[O-].[Na+].[Na+].C(COC)OC>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.O>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([C:17]3[CH:18]=[C:19]([CH3:20])[C:14]([F:13])=[C:15]([CH3:30])[CH:16]=3)=[N:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2418814,7-DichloroquinazolineHCID 569731582-(4-Fluoro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 1212668267-Chloro-4-(4-fluoro-3,5-dimethylphenyl)quinazoline수율 71.1%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

실험 절차

4,7-dichloroquinazoline (4.0 g, 20.1 mmol), 2-(4-fluoro-3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.53 g, 22.1 mmol), sodium carbonate (5.33 g, 50.2 mmol), palladium tetrakis (0.70 g, 0.60 mmol), dimethoxyethane (“DME”) (160 mL), and water (40 mL) were combined in a three neck round bottom flask. A condenser was attached then the system was evacuated and purged with nitrogen three times. The reaction was heated to a vigorous reflux overnight. The reaction was diluted with ethyl acetate, water and brine. The aqueous was partitioned off and the organic was washed once with brine, dried with sodium sulfate, filtered then concentrated down to a yellow solid. The yellow solid was purified with silica gel using DCM to 85/15 DCM/ethyl acetate solvent system to get 4.1 g of light yellow solid for a 71% yield.

후처리

  1. customA condenser was attached
  2. customthe system was evacuated
  3. custompurged with nitrogen three times
  4. temperatureThe reaction was heated to
  5. temperaturea vigorous reflux overnight
  6. additionThe reaction was diluted with ethyl acetate, water and brine
  7. customThe aqueous was partitioned off
  8. washthe organic was washed once with brine
  9. dry with materialdried with sodium sulfate
  10. filtrationfiltered
  11. concentrationthen concentrated down to a yellow solid
  12. customThe yellow solid was purified with silica gel

출처 및 근거

ORD 기록
ord-f2e8d073b0254b32b08c2c4bfa8d35d5
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09397302B2

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