Water → methyl 2-(tert-butoxy)-2-[1-(3,4-dihydro-2H-1-benzopyran-6-yl)thieno[3,2-f]quinolin-2-yl]acetate

HRID 591019노트

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HRID 591019 반응식
C(=O)([O-])[O-].[Na+].[Na+].O.Br[C:9]1[C:13]2=[C:14]3[C:19](=[CH:20][CH:21]=[C:12]2[S:11][C:10]=1[CH:22]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:23]([O:25][CH3:26])=[O:24])[N:18]=[CH:17][CH:16]=[CH:15]3.CC1(C)C(C)(C)OB([C:40]2[CH:41]=[C:42]3[C:47](=[CH:48][CH:49]=2)[O:46][CH2:45][CH2:44][CH2:43]3)O1>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:28]([O:27][CH:22]([C:10]1[S:11][C:12]2[C:13](=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][CH:16]=[CH:15]3)[C:9]=1[C:40]1[CH:49]=[CH:48][C:47]2[O:46][CH2:45][CH2:44][CH2:43][C:42]=2[CH:41]=1)[C:23]([O:25][CH3:26])=[O:24])([CH3:31])([CH3:30])[CH3:29]

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 86717834Methyl 2-{1-bromothieno[3,2-f]quinolin-2-yl}-2-(tert-butoxy)acetate

생성물 1

HCID 70818457methyl 2-(tert-butoxy)-2-[1-(3,4-dihydro-2H-1-benzopyran-6-yl)thieno[3,2-f]quinolin-2-yl]acetate수율 31%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

Under argon atmosphere, sodium carbonate (15.7 mg, 0.15 mmol), water (0.8 mL), and methyl 2-{1-bromothieno[3,2-f]quinolin-2-yl}-2-(tert-butoxy)acetate (16i) (55 mg, 0.14 mmol) were added to a solution of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman (38.5 mg, 0.15 mmol) in N,N-dimethylformamide (3 mL). The solution was degassed under argon and palladium tetrakis(triphenylphosphine) (47 mg, 0.04 mmol) was added. The mixture was heated at 100° C. for 4 hours. The mixture was then cooled at room temperature, water was added and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by preparative TLC (cyclohexane/ethyl acetate 70/30) to afford the desired product (16j) (19 mg, 0.04 mmol, 31%).

후처리

  1. customThe solution was degassed under argon
  2. temperatureThe mixture was then cooled at room temperature
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by preparative TLC (cyclohexane/ethyl acetate 70/30)

출처 및 근거

ORD 기록
ord-44ec1765b5af4e0da350e6daa6753e03
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238026B2

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