Sodium Hydroxide → (R)-tert-butyl 3-(6-(5-(2,6-difluorophenyl)-1H-indol-3-yl)pyrazin-2-yloxy)piperidine-1-carboxylate

HRID 1529301Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14](S(C1C=CC(C)=CC=1)(=O)=O)[CH:13]=[C:12]2[C:28]1[N:33]=[C:32]([O:34][C@@H:35]2[CH2:40][CH2:39][CH2:38][N:37]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:36]2)[CH:31]=[N:30][CH:29]=1.[OH-].[Na+]>O1CCOCC1.O>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[C:28]1[N:33]=[C:32]([O:34][C@@H:35]2[CH2:40][CH2:39][CH2:38][N:37]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:36]2)[CH:31]=[N:30][CH:29]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A glass microwave reaction vessel was charged with (R)-tert-butyl 3-(6-(5-(2,6-difluorophenyl)-1-tosyl-1H-indol-3-yl)pyrazin-2-yloxy)piperidine-1-carboxylate (2.5 g, 3.78 mmol) and NaOH (1.513 mL, 7.57 mmol) in p-dioxane (12 mL). The reaction mixture was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 100° C. for 1 h, then the mixture was diluted with water, and extracted with DCM. The combined organic layers were dried, filtered and concentrated to give the crude (R)-tert-butyl 3-(6-(5-(2,6-difluorophenyl)-1H-indol-3-yl)pyrazin-2-yloxy)piperidine-1-carboxylate.

Workup

customA glass microwave reaction vessel
extractionextracted with DCM
customThe combined organic layers were dried
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-57eba854f4264bdab17a9a6a677b2840
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090593B2

Reaction notes

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