4-(2-Chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)morpholine → 3-(3-chloro-4-(morpholinomethyl)phenyl)-7-(6-morpholinopyridin-3-yl)-9H-carbazole-1-carboxamide

HRID 2410922Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:27]([NH2:29])=[O:28])[C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[C:9]([C:15]1[CH:16]=[N:17][C:18]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:19][CH:20]=1)[CH:8]=3.[Cl:30][C:31]1[CH:43]=[C:42](B2OC(C)(C)C(C)(C)O2)[CH:41]=[CH:40][C:32]=1[CH2:33][N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Cl:30][C:31]1[CH:43]=[C:42]([C:2]2[CH:3]=[C:4]([C:27]([NH2:29])=[O:28])[C:5]3[NH:6][C:7]4[C:12]([C:13]=3[CH:14]=2)=[CH:11][CH:10]=[C:9]([C:15]2[CH:16]=[N:17][C:18]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)=[CH:19][CH:20]=2)[CH:8]=4)[CH:41]=[CH:40][C:32]=1[CH2:33][N:34]1[CH2:35][CH2:36][O:37][CH2:38][CH2:39]1

Participants

Conditions

Temperature: 105 °C

Procedure

To the reaction mixture above (482A) was added 4-(2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)morpholine 477B (0.098 g, 0.289 mmol) and additional PdCl2(dppf)-CH2Cl2 adduct (0.020 g, 0.024 mmol). The mixture was heated in microwave at 105° C. for 1 hr. The mixture was filtered and then purified using preparative HPLC to give titled product. MS (ESI) m/z 582.21 (M+H)+.

Workup

filtrationThe mixture was filtered
custompurified

Sources & evidence

ORD record: ord-fce276f9ef8c48cc957a803bbd744b38
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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