Triethylborane → HCID 9970412, 화합물

HRID 1824804노트

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HRID 1824804 반응식
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:11]=3Br)[S:9][C:5]=2[CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(B(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C=O)C.ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=3)[S:9][C:5]=2[CH:4]=1

참가 물질

7

반응물 4

HCID 7357TriethylboraneHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 22144554HCID 22144554, 화합물

생성물 1

HCID 9970412HCID 9970412, 화합물수율 38.3%

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

To a solution of 6-methoxy-2-(2-bromo-3-methoxy-phenyl)-benzothiazole (0.182, 0.52 mmol) in dry DMF (3 mL) was added cesium carbonate (0.51 g, 1.57 mmol), triethylborane (0.58 mL, 1M in THF, 0.58 mmol) and 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride dichloromethane (18 mg, 0.022 mmol). The mixture was heated to 50° C. for 24 h, then cooled to room temperature. Saturated sodium bicarbonate was added and the mixture was extracted with ethylacetate. Combined ethylacetate were washed with brine, concentrated. After chromatographic purification gave 6-methoxy-2-(3-methoxy-phenyl)-benzothiazole (54 mg, 38% yield) as a white solid. Mass spec: MH+=272.

후처리

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with ethylacetate
  3. washCombined ethylacetate were washed with brine
  4. concentrationconcentrated
  5. customAfter chromatographic purification

출처 및 근거

ORD 기록
ord-028ee8b0118f4ab2b5262db55e64423a
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07045539B2

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