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

HRID 872006Notes

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]

Participants

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

extractionextracted with chloroform
washThe organic layer was washed with water and saturated brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
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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