Bis(2-chloroethyl) ether → 3-bromo-7-morpholino-9H-carbazole-1-carboxamide

HRID 2410909Notes

Reaction equation

[NH2:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[C:8]([Br:18])[CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.Cl[CH2:20][CH2:21][O:22][CH2:23][CH2:24]Cl.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[Br:18][C:8]1[CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]2[NH:12][C:13]3[C:5]([C:6]=2[CH:7]=1)=[CH:4][CH:3]=[C:2]([N:1]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[CH:14]=3

Participants

Conditions

Temperature: 200 °C

Procedure

7-Amino-3-bromo-9H-carbazole-1-carboxamide (250 mg, 0.822 mmol), 1-chloro-2-(2-chloroethoxy)ethane (0.387 mL, 3.29 mmol), sodium carbonate (697 mg, 6.58 mmol) were mixed in DMF (4 mL) in a sealed microwave vial. The vial was degassed and filled with N2. The mixture was heated in microwave at 200° C. for 2 hrs. The mixture was purified using preparative HPLC to give titled product. MS (ESI) m/z 374.01 (M+H)+.

Workup

customThe vial was degassed
additionfilled with N2
customThe mixture was purified

Sources & evidence

ORD record: ord-95b0215c69ef452e8cc349af5c138698
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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