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Sodium Bicarbonate → (2R)-N-{[5-bromo-1-(3-methoxypropyl)indol-3-yl]methyl}-N-cyclopropylmorpholin-2-carboxamide

HRID 872006
Notes
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Reaction equation

HRID 872006 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[C:5]2[CH2:16][N:17]([CH:33]1[CH2:35][CH2:34]1)[C:18]([C@@H:20]1[O:25][CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]1)=[O:19].C(=O)(O)[O-].[Na+]>ClCCCl.[Br-].[Zn+2].[Br-]>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[C:5]2[CH2:16][N:17]([CH:33]1[CH2:35][CH2:34]1)[C:18]([C@@H:20]1[O:25][CH2:24][CH2:23][NH:22][CH2:21]1)=[O:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 59494589HCID 59494589, compound

Product 1

HCID 59494802(2R)-N-{[5-bromo-1-(3-methoxypropyl)indol-3-yl]methyl}-N-cyclopropylmorpholin-2-carboxamide

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

Zinc bromide (209 mg) was added to a solution of tert-butyl(2R)-2-{[{[5-bromo-1-(3-methoxypropyl)indol-3-yl]methyl}(cyclopropyl)amino]carbonyl}morpholin-4-carboxylate (a compound of Reference Example 128, 200 mg) in 1,2-dichloroethane (12 ml) and the mixture was stirred at 40° C. for 3 hours. The reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and extracted with chloroform. The organic layer was washed with water and saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: chloroform/methanol=98/2 to 93/7) to give (2R)—N-{[5-bromo-1-(3-methoxypropyl)indol-3-yl]methyl}-N-cyclopropylmorpholin-2-carboxamide (117 mg) as a colorless oil.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulted residue was purified with a silica gel column chromatography (eluting solvent: chloroform/methanol=98/2 to 93/7)

Sources & evidence

ORD record
ord-2da09ada2c9140af8df81b64e5c246cb
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08975252B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes