Sodium Carbonate → Tert-butyl (2e)-3-(4-amino-3-bromothieno[3,2-c]pyridin-7-yl)acrylate

HRID 17144

반응식

HRID 17144 반응식
[Br:1][C:2]1[C:6]2[C:7]([NH2:12])=[N:8][CH:9]=[C:10](I)[C:5]=2[S:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Na+].[Na+].[C:38]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])(=[O:41])[CH:39]=[CH2:40]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:12][C:7]1[C:6]2[C:2]([Br:1])=[CH:3][S:4][C:5]=2[C:10](/[CH:40]=[CH:39]/[C:38]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[CH:9][N:8]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 15458tert-Butyl acrylateHCID 184507913-Bromo-7-iodothieno[3,2-C]pyridin-4-amine

생성물 1

HCID 18451450Tert-butyl (2e)-3-(4-amino-3-bromothieno[3,2-c]pyridin-7-yl)acrylate수율 42.8%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

A solution of Example 21A (2.50 g, 7.04 mmol), PPh3 (0.370 g, 1.41 mmol), and Na2CO3 (1.49 g, 14.1 mmol) in DMF (35 mL) was treated with tert-butyl acrylate (2.00 mL, 14.1 mmol) and palladium(II)acetate (0.158 g, 0.704 mmol). The reaction was heated to 80° C. under an atmosphere of nitrogen for 16 hours. The reaction was cooled to ambient temperature and partitioned between ethyl acetate (100 mL) and brine. The organic phase was washed with brine (2×100 mL), dried (Na2SO4), filtered, and concentrated. The compound was purified by flash chromatography on silica gel using heptane/ethyl acetate (6:1) to (3:1) to provide the desired product (1.70 g, 3.01 mmol). 1HNMR (DMSO-d6, 400MHz) δ 8.24 (s, 1H), 7.94 (s, 1H), 7.62 (d, 1H), 7.17 (br s, 2H), 6.22 (d, 1H), 1.48 (s, 9H); MS m/e 355/357 (M+H)+.

후처리

  1. temperatureThe reaction was cooled to ambient temperature
  2. custompartitioned between ethyl acetate (100 mL) and brine
  3. washThe organic phase was washed with brine (2×100 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe compound was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-e1b0546f08de4b4e964df24b8397f34b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737160B2

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