Water → tert-butyl 3-((6-(2-methoxy-4-(1H-pyrazol-1-yl)phenyl)pyridazin-3-yl)oxy)pyrrolidine-1-carboxylate

HRID 1027187Notes

Reaction equation

CC(C)([O-])C.[K+].[OH:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]1.Cl[C:21]1[N:22]=[N:23][C:24]([C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH:37]=[CH:36][CH:35]=[N:34]3)=[CH:29][C:28]=2[O:38][CH3:39])=[CH:25][CH:26]=1.O>C1COCC1>[CH3:39][O:38][C:28]1[CH:29]=[C:30]([N:33]2[CH:37]=[CH:36][CH:35]=[N:34]2)[CH:31]=[CH:32][C:27]=1[C:24]1[N:23]=[N:22][C:21]([O:7][CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]2)=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Potassium tert-butoxide (1.0 M in THF, 0.98 mL, 0.98 mmol) was added to tert-butyl 3-hydroxypyrrolidine-1-carboxylate (0.18 g, 0.98 mmol) in THF (3.3 mL) at 0° C. and the mixture was stirred for 10 min at 50° C. 3-Chloro-6-(2-methoxy-4-(1H-pyrazol-1-yl)phenyl)pyridazine Intermediate 2-1 (0.12 g, 0.40 mmol) was added to the reaction at 0° C. and the mixture was stirred for 2 h at RT. Water (0.1 mL) was added and the solvent was concentrated under reduced pressure to afford (0.18 g, 100%) of a brown solid.

Workup

stirringthe mixture was stirred for 2 h at RT
concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record: ord-fa0bac9cbb4b48d389a577def4324bdf
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729263B2

Reaction notes

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