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Sodium hydride → (+/-)-tert-butyl-1-(3-(2-methoxyethoxy)butan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

HRID 1527055
ノート
印刷プレビュー

反応式

HRID 1527055 の反応式
[H-].[Na+].[OH:3][CH:4]([CH3:24])[CH:5]([N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[C:9]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[C:8]1[CH3:23])[CH3:6].Br[CH2:26][CH2:27][O:28][CH3:29]>[Cl-].[Na+].O>[C:19]([O:18][C:16]([C:9]1[C:10]2[C:11](=[N:12][CH:13]=[CH:14][CH:15]=2)[N:7]([CH:5]([CH:4]([O:3][CH2:26][CH2:27][O:28][CH3:29])[CH3:24])[CH3:6])[C:8]=1[CH3:23])=[O:17])([CH3:22])([CH3:21])[CH3:20]
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 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 89740048tert-butyl 1-(3-hydroxybutan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

生成物 1

HCID 117779040(+/-)-tert-butyl-1-(3-(2-methoxyethoxy)butan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

試薬・触媒・溶媒 1

HCID 57417360Sodium chloride; water溶媒

反応条件

温度
40 °C

実験手順

Sodium hydride (0.026 g, 0.657 mmol) and (±)-tert-butyl 1-(3-hydroxybutan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (0.1 g, 0.329 mmol) were added to a 25 mL rbf and the atmosphere was purged with N2. DMF (5 mL) was added and the reaction was heated at 40° C. for 1 h. The reaction was cooled to ambient temperature and 1-bromo-2-methoxyethane (0.062 ml, 0.657 mmol) was added. The reaction was heated at 90° C. for 3 d. LCMS showed ˜60% conversion. The reaction was poured into half-saturated brine, extracted with EtOAc, the org layer was washed with half-saturated brine, brine, filtered, concentrated and loaded onto a column with aid of DCM. 2×12 g column, the column was then treated with 2 CV of Hex then 20% EtAOc in Hex to elute (±)-tert-butyl 1-(3-(2-methoxyethoxy)butan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (44.4 mg, 37.3%). LRMS (M+H+) m/z: calcd 363.46. found 363.1.

後処理

  1. customthe atmosphere was purged with N2
  2. additionDMF (5 mL) was added
  3. temperatureThe reaction was cooled to ambient temperature
  4. temperatureThe reaction was heated at 90° C. for 3 d
  5. extractionextracted with EtOAc
  6. washthe org layer was washed with half-saturated brine, brine
  7. filtrationfiltered
  8. concentrationconcentrated
  9. addition2×12 g column, the column was then treated with 2 CV of Hex
  10. wash20% EtAOc in Hex to elute (±)-tert-butyl 1-(3-(2-methoxyethoxy)butan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (44.4 mg, 37.3%)

出典と根拠

ORDレコード
ord-22870e767f0b495f88a24a6dd4fc6bc0
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09085583B2

反応ノート

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