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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 2206568
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HRID 2206568 반응식
[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]
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참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 57417360Sodium chloride; water용매

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온도
40 °C

실험 절차

Sodium hydride (0.026 g, 0.657 mmol) and (±)-tert-butyl 1-(3-hydroxybutan-2-yl)-2-methyl-1 H-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 2CV of Hex then 20% EtAOc in Hex to elute (±)-tert-butyl 1-(3-(2-methoxyethoxyl)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.

후처리

  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 2CV of Hex
  10. wash20% EtAOc in Hex to elute (±)-tert-butyl 1-(3-(2-methoxyethoxyl)butan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (44.4 mg, 37.3%)

출처 및 근거

ORD 기록
ord-4b31e456bcf349da8b9ae36d8f34b3c5
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09371331B2

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