Piperidine → (Z)-2-[(1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-methoxy-7-(morpholinomethyl)benzofuran-3(2H)-one

HRID 1749829Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7](=[O:10])[CH2:8][O:9][C:5]=2[C:4]=1[CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][N:27]=2)[C:22]([CH:29]=O)=N1.N1CCCC[CH2:32]1>CO>[NH:20]1[C:28]2=[N:27][CH:26]=[CH:25][CH:24]=[C:23]2[C:22](/[CH:29]=[C:8]2\[O:9][C:5]3[C:4]([CH2:13][N:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:6]=3[C:7]\2=[O:10])=[CH:32]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 6-methoxy-7-(morpholinomethyl)benzofuran-3(2H)-one (0.131 g, 0.500 mmol) obtained in Example A41, Step 2 in methanol (1.2 mL) was added with 7-aza-1H-indazole-3-carboxaldehyde (0.0545 g, 0.373 mmol) and piperidine (0.00265 g, 0.0311 mmol), and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was cooled to room temperature, and then added with methanol (2 mL), and the precipitated solid was suspended in methanol and thereby washed to obtain the objective (Z)-2-[(1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-methoxy-7-(morpholinomethyl)benzofuran-3(2H)-one (0.0264 g, 21%).

Workup

temperatureThe reaction mixture was cooled to room temperature
washwashed

Sources & evidence

ORD record: ord-193a30b09f3447bca49bd1cab3619f5c
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156827B2

Reaction notes

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