1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-chloro-3-methyl-8-((1-methylpiperidin-4-yl)methoxy)-9H-pyrido[2,3-b]indole

HRID 1642560Notes

Reaction equation

Br[C:2]1[C:3]([NH:9][C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[O:17][CH2:18][CH:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.C1CCN2C(=NCCC2)CC1>CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C>[Cl:16][C:14]1[CH:13]=[CH:12][C:11]([O:17][CH2:18][CH:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)=[C:10]2[C:15]=1[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[N:4][C:3]=1[NH:9]2

Participants

Conditions

Temperature: 155 °C

Procedure

To a stirred solution of Compound 174 (450 mg, 1.06 mmol) in anhydrous and degassed DMF (3 mL), were added Pd(OAc)2 (59 mg, 0.26 mmol) and DBU (0.48 mL, 3.18 mmol), under nitrogen. After being stirred for 6 h. at 155° C. the reaction was quenched by addition of water (5 mL). The solid precipitates out was filtered and washed thoroughly with water. The residue was dried under vacuum and purified by flash chromatography to furnish Compound 175 (237 mg, 65%).

Workup

customwas quenched by addition of water (5 mL)
customThe solid precipitates
filtrationout was filtered
washwashed thoroughly with water
customThe residue was dried under vacuum
custompurified by flash chromatography

Sources & evidence

ORD record: ord-a911335e236c4f149cdc675bb2ddfbca
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119655B2

Reaction notes

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