Sodium Carbonate → 7-(Morpholine-4-carbonyl)-2-(4-morpholinophenyl)-5H-pyrido[3,2-b]indole-4-carboxamide

HRID 2410903Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:23]([NH2:25])=[O:24])[C:5]2[NH:6][C:7]3[CH:8]=[C:9]([C:15]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[O:16])[CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1.CC1(C)C(C)(C)OB([C:34]2[CH:39]=[CH:38][C:37]([N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)=[CH:36][CH:35]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>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.COCCOC>[N:17]1([C:15]([C:9]2[CH:10]=[CH:11][C:12]3[C:13]4[N:14]=[C:2]([C:34]5[CH:35]=[CH:36][C:37]([N:40]6[CH2:41][CH2:42][O:43][CH2:44][CH2:45]6)=[CH:38][CH:39]=5)[CH:3]=[C:4]([C:23]([NH2:25])=[O:24])[C:5]=4[NH:6][C:7]=3[CH:8]=2)=[O:16])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

Conditions

Temperature: 100 °C

Procedure

2-Bromo-7-(morpholine-4-carbonyl)-5H-pyrido[3,2-b]indole-4-carboxamide (60 mg, 0.149 mmol), 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine (86 mg, 0.298 mmol), PdCl2(dppf)-CH2Cl2 adduct (12.15 mg, 0.015 mmol), and Na2CO3 (2M) (0.223 mL, 0.446 mmol) were mixed with DME (4 mL) in a sealed microwave vial. The mixture was flushed with N2 and heated at 100° C. in an oil bath for 4 hrs. The mixture was concentrated and purified using preparative HPLC to give titled product. MS (ESI) m/z 486.13 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.65 (s, 1H), 8.63 (s, 1H), 8.4 (s, 1H), 8.29 (d, 1H, J=7.9), 8.20 (d, 2H, J=8.9), 7.9 (s, 1H), 7.79 (s, 1H), 7.29(dd, 1H, J=8.0, 1.5), 7.11 (d, 2H, J=9.2), 3.79 (t, 4H, J=4.9), 3.65-3.45 (bm, 8H), 3.23 (t, 4H, J=4.9).

Workup

customThe mixture was flushed with N2
concentrationThe mixture was concentrated
custompurified

Sources & evidence

ORD record: ord-7613fa4352ab4047a931af33f1ac801b
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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