5-chloro-3-iodo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine → (5-Chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[2-fluoro-5-methoxy-4-(1-methyl-1H-benzoimidazol-2-ylmethoxy)-phenyl]-methanol

HRID 253462

반응식

HRID 253462 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[CH:9][N:8]([Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])[C:5]2=[N:6][CH:7]=1.C([Mg]Cl)(C)C.[F:27][C:28]1[CH:35]=[C:34]([O:36][CH2:37][C:38]2[N:42]([CH3:43])[C:41]3[CH:44]=[CH:45][CH:46]=[CH:47][C:40]=3[N:39]=2)[C:33]([O:48][CH3:49])=[CH:32][C:29]=1[CH:30]=[O:31]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([CH:30]([C:29]3[CH:32]=[C:33]([O:48][CH3:49])[C:34]([O:36][CH2:37][C:38]4[N:42]([CH3:43])[C:41]5[CH:44]=[CH:45][CH:46]=[CH:47][C:40]=5[N:39]=4)=[CH:35][C:28]=3[F:27])[OH:31])=[CH:9][N:8]([Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])[C:5]2=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 580879285-chloro-3-iodo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridineHCID 598038732-fluoro-5-methoxy-4-(1-methyl-1H-benzimidazol-2-ylmethoxy)-benzaldehydeHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 66888056(5-Chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-[2-fluoro-5-methoxy-4-(1-methyl-1H-benzoimidazol-2-ylmethoxy)-phenyl]-methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-25 °C

실험 절차

5-Chloro-3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (144, 0.235 g, 0.541 mmol, prepared as described in Example 49) was dissolved in tetrahydrofuran (5 mL, 60 mmol). The solution was cooled to −25° C. After the addition of 2 M of isopropylmagnesium chloride in tetrahydrofuran (400 μL) the reaction was warmed to −10° C. with stirring. The reaction was cooled to −30° C. and 2-fluoro-5-methoxy-4-(1-methyl-1H-benzimidazol-2-ylmethoxy)-benzaldehyde (143, 0.170 g, 0.541 mmol) in 4 mL of tetrahydrofuran was added at once to the mixture. The reaction warmed to −10° C. and then evaporated to dryness. Ethyl acetate was added and the organic portion was washed with saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate and concentrated. Purification with silica gel flash chromatography with a gradient of ethyl acetate (5 to 80%) in hexanes gave the desired compound 145.

후처리

  1. temperaturewas warmed to −10° C.
  2. temperatureThe reaction was cooled to −30° C.
  3. temperatureThe reaction warmed to −10° C.
  4. customevaporated to dryness
  5. additionEthyl acetate was added
  6. washthe organic portion was washed with saturated sodium bicarbonate solution and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customPurification with silica gel flash chromatography with a gradient of ethyl acetate (5 to 80%) in hexanes

출처 및 근거

ORD 기록
ord-188f16f3a0b247b58f64d9b468716e79
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872018B2

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