Triethylborane → HCID 9970412、化合物

HRID 1824804ノート

反応式

HRID 1824804 の反応式
[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

参加物

7

反応物 4

HCID 7357TriethylboraneHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 22144554HCID 22144554、化合物

生成物 1

HCID 9970412HCID 9970412、化合物収率 38.3%

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-028ee8b0118f4ab2b5262db55e64423a
出典データセット
uspto-grants-2006_05
特許番号
US07045539B2

反応ノート

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