6-Methyl-1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde → tert-butyl (Z)-4-({5-chloro-6-hydroxy-2-[(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate

HRID 1749823Notes

Reaction equation

[Cl:1][C:2]1[C:3]([OH:26])=[C:4]([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[C:5]2[O:9][CH2:8][C:7](=[O:10])[C:6]=2[CH:11]=1.[CH3:27][C:28]1[N:33]=[C:32]2[NH:34][CH:35]=[C:36]([CH:37]=O)[C:31]2=[CH:30][CH:29]=1>CO.N1CCCCC1>[Cl:1][C:2]1[C:3]([OH:26])=[C:4]([CH2:12][N:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:15][CH2:14]2)[C:5]2[O:9]/[C:8](=[CH:37]\[C:36]3[C:31]4[C:32](=[N:33][C:28]([CH3:27])=[CH:29][CH:30]=4)[NH:34][CH:35]=3)/[C:7](=[O:10])[C:6]=2[CH:11]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of tert-butyl 4-[(5-chloro-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.012 g, 0.031 mmol) obtained in Example A12, Step 2 in methanol (2.0 mL) was added with 6-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde (0.005 g, 0.028 mmol) obtained in Example A48, Step 4. Then, the mixture was added with 5 drops of piperidine, and then the mixture was stirred at 50° C. for 3 hours. The solvent was evaporated under reduced pressure, and then the residue was suspended in diethyl ether and thereby washed to obtain tert-butyl (Z)-4-({5-chloro-6-hydroxy-2-[(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.010 g, 68%).

Workup

customThe solvent was evaporated under reduced pressure
washwashed

Sources & evidence

ORD record: ord-165def68cd954f908ecbdb68041de4aa
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156827B2

Reaction notes

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