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Methanamine, N-methoxy-, hydrochloride (1:1) → (+/-)-tert-butyl 1-(1-(methoxy(methyl)amino)-1-oxopropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

HRID 2206566
Notes
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Reaction equation

HRID 2206566 reaction equation
CO[C:3](=[O:23])[CH:4]([N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[C:7]1[CH3:22])[CH3:5].Cl.[CH3:25][NH:26][O:27][CH3:28].C([Mg]Cl)(C)C>>[CH3:28][O:27][N:26]([CH3:25])[C:3](=[O:23])[CH:4]([N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8]([C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])=[C:7]1[CH3:22])[CH3:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 117779095(+/-)-tert-butyl 1-(1-methoxy-1-oxopropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylateHCID 178418918HCID 178418918, compound

Product 1

HCID 117779094(+/-)-tert-butyl 1-(1-(methoxy(methyl)amino)-1-oxopropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylateYield 60.3%

Conditions

Temperature
0 °C

Procedure

To a 100 mL round-bottom flask was added (±)-tert-butyl 1-(1-methoxy-1-oxopropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (0.958 g, 3.01 mmol) and N,O-dimethylhydroxylamine hydrochloride (0.440 g, 4.51 mmol). The flask was vac/purged 3× with N2 then THF (17 mL) were added and the reaction was cooled to −40° C. isopropylmagnesium chloride (4.51 ml, 9.03 mmol) was added dropwise and the reaction was mixed at that temperature for 1 h then warmed to 0° C. for 1 h then quenched with 1N HCl, extracted with EtOAc. The org layer was washed with water then brine, dried over Na2SO4, filtered, concentrated, deposited onto silica gel with aid of DCM, and purified by CC using 25% EtOAc in Hex as eluent to provide (±)-tert-butyl 1-(1-(methoxy(methyl)amino)-1-oxopropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (0.630 g, 60.3%). LRMS (M+H+) m/z: calcd 348.41. found 348.2.

Workup

  1. customThe flask was vac/purged 3× with N2
  2. additionTHF (17 mL) were added
  3. additionwas added dropwise
  4. additionthe reaction was mixed at that temperature for 1 h
  5. customthen quenched with 1N HCl
  6. extractionextracted with EtOAc
  7. washThe org layer was washed with water
  8. dry with materialbrine, dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified by CC

Sources & evidence

ORD record
ord-b33217acc7f24b3ead6e981281077d3a
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