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

反応式

HRID 253462 の反応式
[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

参加物

5

反応物 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、化合物

生成物 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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-188f16f3a0b247b58f64d9b468716e79
出典データセット
uspto-grants-2011_01
特許番号
US07872018B2

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