Water → (4-Benzyloxy-2-fluoro-5-methoxy-phenyl)-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol

HRID 253417

反応式

HRID 253417 の反応式
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:3]=1.C([Mg]Cl)(C)C.[CH2:26]([O:33][C:34]1[C:41]([O:42][CH3:43])=[CH:40][C:37]([CH:38]=[O:39])=[C:36]([F:44])[CH:35]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>O1CCCC1>[CH2:26]([O:33][C:34]1[C:41]([O:42][CH3:43])=[CH:40][C:37]([CH:38]([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[N:4]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:3]=2)[OH:39])=[C:36]([F:44])[CH:35]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

参加物

6

反応物 4

HCID 962WaterHCID 5614564-Benzyloxy-2-fluoro-5-methoxy-benzaldehydeHCID 242292273-Iodo-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridineHCID 178418918HCID 178418918、化合物

生成物 1

HCID 58087295(4-Benzyloxy-2-fluoro-5-methoxy-phenyl)-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol収率 97.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

3-Iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (68, 620 mg, 1.5 mmol, prepared as described in Example 22) was dissolved in tetrahydrofuran (15 mL) at −20° C. under an atmosphere of nitrogen. Isopropylmagnesium chloride (2.0 M in tetrahydrofuran, 840 μL) was added to the reaction. The reaction was stirred for 1.5 hours, during which the temperature rose to 5° C. The reaction was cooled to −20° C. 4-Benzyloxy-2-fluoro-5-methoxy-benzaldehyde (83, 250 mg, 0.9606 mmol) in tetrahydrofuran (5.0 mL) was added to the reaction. The reaction was stirred for 2.5 hours during which time the temperature rose to 5° C. The reaction was poured into water. The mixture was extracted with ethyl acetate. The organic layer was dried over an hydrous sodium sulfate, and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 2-25% ethyl acetate in hexane to provide compound as a white solid (84, 501 mg, 63%). MS (ESI) [M+H+]+=535.4.

後処理

  1. customrose to 5° C
  2. stirringThe reaction was stirred for 2.5 hours during which time the temperature
  3. customrose to 5° C
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over an hydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. custompurified by silica gel column chromatography
  9. washeluting with 2-25% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-6d695476114d42e58f9fa197eb106b75
出典データセット
uspto-grants-2011_01
特許番号
US07872018B2

関連ノート

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