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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
Notes
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Reaction equation

HRID 2206568 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 57417360
Sodium chloride; water
Solvent

Conditions

Temperature
40 °C

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-4b31e456bcf349da8b9ae36d8f34b3c5
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09371331B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes