Ethanol → HCID 58111865, compound

HRID 1667634Notes

Reaction equation

[C:1]([O:5][C:6](=[O:35])[N:7]([C@H:9]([C:11](=[O:34])[NH:12][C@@H:13]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]1[CH:22]=[N:23][CH:24]=[C:25](Br)[CH:26]=1)=[O:15])[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[C:36]([O-:39])([O-])=[O:37].[Na+].[Na+].[C:42]1(C)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C(O)C>CCOC(C)=O>[C:1]([O:5][C:6](=[O:35])[N:7]([C@H:9]([C:11](=[O:34])[NH:12][C@@H:13]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]1[CH:22]=[N:23][CH:24]=[C:25]([C:42]2[CH:47]=[CH:46][C:45]3[O:37][CH2:36][O:39][C:44]=3[CH:43]=2)[CH:26]=1)=[O:15])[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

The mixture of ((S)-1-{(S)-2-[(S)-2-(5-Bromo-pyridin-3-yl)-pyrrolidin-1-yl]-1-cyclohexyl-2-oxo-ethylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester 5 (168 mg, 0.31 mmole), 3,4-(methylene dioxy)pheny boronic acid (60.7 mg, 0.37 mmole), Na2CO3 (1.8 mL, 1.8 momle, 1 M aqueous) in a mixed solution of 8 mL of toluene and 3 mL of ethanol was degaseq under vacuum. After heat at 80° C. for 1.5 hours, the reaction mixture was cooled to room temperature and diluted with 30 mL of EtOAc, and washed by 3×15 mL of water. The organic layer was filtered and concentrated to give 3-(5-{(S)-1-[1-(4-Methoxy-phenyl)-ethyl]-pyrrolidin-2-yl}-pyridin-3-yl)-indole-1-carboxylic acid tert-butyl ester 6 as crude producte without further purification for next step reaction.

Workup

temperaturethe reaction mixture was cooled to room temperature
washwashed by 3×15 mL of water
filtrationThe organic layer was filtered
concentrationconcentrated

Sources & evidence

ORD record: ord-01ae541dc90641abb0925f80a7d19bfe
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044209B2

Reaction notes

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