Bromobenzene → Ethyl 3,4-dihydro-4-phenyl-2H-1,4-benzoxazine-2-carboxylate

HRID 253111

반응식

HRID 253111 반응식
CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.Br[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.[O:50]1[CH:55]([C:56]([O:58][CH2:59][CH3:60])=[O:57])[CH2:54][NH:53][C:52]2[CH:61]=[CH:62][CH:63]=[CH:64][C:51]1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:44]1([N:53]2[CH2:54][CH:55]([C:56]([O:58][CH2:59][CH3:60])=[O:57])[O:50][C:51]3[CH:64]=[CH:63][CH:62]=[CH:61][C:52]2=3)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

참가 물질

8

반응물 4

HCID 7961BromobenzeneHCID 10796Cesium carbonateHCID 31090Ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

생성물 1

HCID 86614014Ethyl 3,4-dihydro-4-phenyl-2H-1,4-benzoxazine-2-carboxylate

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

Tris(dibenzylideneacetone)dipalladium (0) (4.3 mg, 0.0046 mmol), xantphos (8.2 mg, 0.014 mmol), and bromobenzene (40 □L, 0.381 mmol) were added to a solution of (±)-ethyl 3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylate (65 mg, 0.31 mmol) in dioxane (2.5 mL). The solids were allowed to dissolve, and cesium carbonate (143 mg, 0.44 mmol) was added, and the suspension was stirred at 100° C. for 24 h. The mixture was cooled to ambient temperature, diluted with water (20 mL), and the product was extracted with 67% EtOAc/hexane (3×25 mL). The organic layers were combined, dried over sodium sulfate, and concentrated. Purification of the crude concentrate by flash column chromatography using 15% EtOAc/hexane afforded the title compound. MS m/z: 284 (M+1).

후처리

  1. dissolutionto dissolve
  2. temperatureThe mixture was cooled to ambient temperature
  3. extractionthe product was extracted with 67% EtOAc/hexane (3×25 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification of the crude
  7. concentrationconcentrate by flash column chromatography

출처 및 근거

ORD 기록
ord-378c8d6cc1b242259dac99d498f4cb3c
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872009B2

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