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

HRID 1966685

반응식

HRID 1966685 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e10d6363990b4126980d57e36b3d770c
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420655B2

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