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1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-3-iodo-1H-pyrrolo[3,2-c]pyridine → [1-(2-{[tert-butyl(methyl)silyl]oxyl}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl](4-chloropyridin-2-yl)methanone

HRID 1753054
ノート
印刷プレビュー

反応式

HRID 1753054 の反応式
[Si:1]([O:8][CH2:9][C:10]([N:13]1[C:21]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[C:15](I)=[CH:14]1)([CH3:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])(C)[CH3:2].C([Mg]Cl)(C)C.[Cl:28][C:29]1[CH:34]=[CH:33][N:32]=[C:31]([C:35](NOC)=[O:36])[C:30]=1C>C1COCC1>[C:4]([SiH:1]([CH3:2])[O:8][CH2:9][C:10]([N:13]1[C:21]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[C:15]([C:35]([C:31]2[CH:30]=[C:29]([Cl:28])[CH:34]=[CH:33][N:32]=2)=[O:36])=[CH:14]1)([CH3:11])[CH3:12])([CH3:5])([CH3:6])[CH3:7]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 900934361-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-3-iodo-1H-pyrrolo[3,2-c]pyridineHCID 900937914-chloro-N-methoxy-M-methylpicolinamideHCID 178418918HCID 178418918、化合物

生成物 1

HCID 137331321[1-(2-{[tert-butyl(methyl)silyl]oxyl}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl](4-chloropyridin-2-yl)methanone収率 60.8%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
3 回

反応条件

温度
-5 °C

実験手順

1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-3-iodo-1H-pyrrolo[3,2-c]pyridine (Preparation 65, 3.99 g, 9.06 mmol) was dissolved in THF (75 mL) and the solution was degassed and cooled to −5° C. 2M iPrMgCl in THF (5.44 mL, 10.9 mmol) was added dropwise and the resulting yellow solution stirred at this temperature for 45 minutes. A solution of 4-chloro-N-methoxy-M-methylpicolinamide (2.18 g, 10.9 mmol) in THF (20 mL) was added dropwise and the reaction allowed to warm to room temperature for 4.5 hours. The reaction was partitioned between saturated aqueous ammonium chloride solution (30 mL) and EtOAc (50 mL), the organic layer was collected, dried and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 0-90% EtOAc in DCM to afford the title compound as an orange oil (2.37 g, 59%). Taken on to the next step directly.

後処理

  1. customthe solution was degassed
  2. temperatureto warm to room temperature for 4.5 hours
  3. customThe reaction was partitioned between saturated aqueous ammonium chloride solution (30 mL) and EtOAc (50 mL)
  4. customthe organic layer was collected
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified
  8. washeluting with 0-90% EtOAc in DCM

出典と根拠

ORDレコード
ord-b20284d6cfa7497f97132974f2aeadcc
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09163021B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート