Water → methyl 2-(tert-butoxy)-2-[5-(3,4-dihydro-2H-1-benzopyran-6-yl)-2-phenyl-1,3-thiazol-4-yl]acetate

HRID 590972노트

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HRID 590972 반응식
C(=O)([O-])[O-].[Na+].[Na+].O.CC1(C)C(C)(C)OB([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[O:22][CH2:21][CH2:20][CH2:19]3)O1.Br[C:28]1[S:32][C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:30][C:29]=1[CH:39]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])[C:40]([O:42][CH3:43])=[O:41]>CN(C)C=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:45]([O:44][CH:39]([C:29]1[N:30]=[C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[S:32][C:28]=1[C:16]1[CH:25]=[CH:24][C:23]2[O:22][CH2:21][CH2:20][CH2:19][C:18]=2[CH:17]=1)[C:40]([O:42][CH3:43])=[O:41])([CH3:48])([CH3:46])[CH3:47]

참가 물질

7

반응물 4

HCID 962Water2회HCID 10340Sodium CarbonateHCID 438110342-(3,4-dihydro-2H-1-benzopyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 70819454Methyl 2-(5-bromo-2-phenyl-1,3-thiazol-4-yl)-2-(tert-butoxy)acetate

생성물 1

HCID 70855246methyl 2-(tert-butoxy)-2-[5-(3,4-dihydro-2H-1-benzopyran-6-yl)-2-phenyl-1,3-thiazol-4-yl]acetate수율 70.5%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

Under a nitrogen atmosphere, sodium carbonate (8.5 mg, 0.08 mmol), water (500 μL), palladium tetrakis(triphenylphosphine) (13 mg, 0.012 mmol) and 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman (21 mg, 0.078 mmol) were added to a solution of methyl 2-(5-bromo-2-phenyl-1,3-thiazol-4-yl)-2-(tert-butoxy)acetate (30 mg, 0.078 mmol) in N,N-dimethylformamide (2 mL). The mixture was heated at 120° C. for 2 hours. The mixture was then cooled at room temperature and water (10 mL) was added. The aqueous layer was extracted with ethyl acetate (2×10 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired product (6d) as a white solid (24 mg, 0.055 mmol, 70%).

후처리

  1. temperatureThe mixture was then cooled at room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×10 mL)
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10)

출처 및 근거

ORD 기록
ord-46e6e992c5264b3c8b4a8f8bf0762dd6
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238026B2

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