Potassium Carbonate → 2-(2,4-Dimethyl-thiazol-5-yl)-5-methoxy-benzaldehyde

HRID 1966685

反応式

HRID 1966685 の反応式
Br[C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:12][C:13]1[S:14][C:15](B2OC(C)(C)C(C)(C)O2)=[C:16]([CH3:18])[N:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.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>[CH3:12][C:13]1[S:14][C:15]([C:2]2[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=2[CH:4]=[O:5])=[C:16]([CH3:18])[N:17]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 3444802-Bromo-5-methoxybenzaldehydeHCID 185257002,4-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole

生成物 1

HCID 585420022-(2,4-Dimethyl-thiazol-5-yl)-5-methoxy-benzaldehyde収率 65.2%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

To a solution of 2-bromo-5-methoxybenzaldehyde (200 mg, 0.93 mmol) in DMF (10 mL) and H2O (2 mL) are added 2,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole (333 mg, 1.4 mmol), Pd(PPh3)4 (107 mg, 0.09 mmol) and K2CO3 (257 mg, 1.9 mmol) at room temperature. The solution is heated to 120° C. for 1 hour in a microwave reactor. The solution is cooled down and 3-mercaptopropyl-functionalized silica gel (500 mg) is added. The solution is stirred for 15 minutes and is filtered. The filtrate is washed with H2O (10 mL) and is extracted with EtOAc (3×10 mL). The combined organic layer is dried, (MgSO4), filtered and is concentrated and the residue is purified by silica gel flash chromatography eluting with 50% EtOAc in heptane to afford 2-(2,4-Dimethyl-thiazol-5-yl)-5-methoxy-benzaldehyde (150 mg, 65%) as a white foam.

後処理

  1. temperatureThe solution is cooled down
  2. addition3-mercaptopropyl-functionalized silica gel (500 mg) is added
  3. filtrationis filtered
  4. washThe filtrate is washed with H2O (10 mL)
  5. extractionis extracted with EtOAc (3×10 mL)
  6. dry with materialThe combined organic layer is dried, (MgSO4),
  7. filtrationfiltered
  8. concentrationis concentrated
  9. customthe residue is purified by silica gel flash chromatography
  10. washeluting with 50% EtOAc in heptane

出典と根拠

ORDレコード
ord-e10d6363990b4126980d57e36b3d770c
出典データセット
uspto-grants-2013_04
特許番号
US08420655B2

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