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Sodium hydride → tert-Butyl-4-((6-(5-(3-isopropyl-1,2,4-oxadiazol-5-yl)-1H-indol-1-yl) pyridin-3-yl) oxy)piperidine-1-carboxylate

HRID 1468039
Notes
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Reaction equation

HRID 1468039 reaction equation
[OH:1][N:2]=[C:3]([NH2:7])[CH:4]([CH3:6])[CH3:5].[H-].[Na+].C(O[C:13]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH:31]3[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]3)=[CH:26][N:25]=1)[CH:19]=[CH:18]2)=O)C>C1COCC1>[C:40]([O:39][C:37]([N:34]1[CH2:33][CH2:32][CH:31]([O:30][C:27]2[CH:26]=[N:25][C:24]([N:20]3[C:21]4[C:17](=[CH:16][C:15]([C:13]5[O:1][N:2]=[C:3]([CH:4]([CH3:6])[CH3:5])[N:7]=5)=[CH:23][CH:22]=4)[CH:18]=[CH:19]3)=[CH:29][CH:28]=2)[CH2:36][CH2:35]1)=[O:38])([CH3:43])([CH3:42])[CH3:41]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2794833N'-Hydroxy-2-methylpropanimidamideHCID 67617454Ethyl-1-(5-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)pyridin-2-yl)-1H-indole-5-carboxylate

Product 1

HCID 86696203tert-Butyl-4-((6-(5-(3-isopropyl-1,2,4-oxadiazol-5-yl)-1H-indol-1-yl) pyridin-3-yl) oxy)piperidine-1-carboxylateYield 22.6%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of N′-hydroxyisobutyrimidamide (0.10 g, 1.0 mmol) in dry THF (10 mL), NaH (0.078 g, 3.26 mmol) was added and stirred at 60° C. for 2 h. The reaction contents were brought to room temperature, Ethyl-1-(5-((1-(tert-butoxycarbonyl)piperidin-4-yl) oxy) pyridin-2-yl)-1H-indole-5-carboxylate (0.205 g, 0.440 mmol) was added and stirred at 60° C. for 3 h. The reaction was quenched by methanol at 0° C. and concentrated in vacuo. The resultant residue was dissolved with ethyl acetate and washed with water, the organic layer was separated, concentrated in vacuo and the resulting residue was purified by flash column chromatography to give the title compound (0.050 g, 10.16%).

Workup

  1. customThe reaction contents
  2. customwere brought to room temperature
  3. stirringstirred at 60° C. for 3 h
  4. customThe reaction was quenched by methanol at 0° C.
  5. concentrationconcentrated in vacuo
  6. dissolutionThe resultant residue was dissolved with ethyl acetate
  7. washwashed with water
  8. customthe organic layer was separated
  9. concentrationconcentrated in vacuo
  10. customthe resulting residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-ad749111d6bf40018f909b945ab7139d
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09000175B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes