Potassium Carbonate → 6-(4-methoxyphenyl)-3-(morpholine-4-carbonyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide

HRID 2410659Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([C:15]([NH2:17])=[O:16])[CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH:7]([C:18]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:19])[CH2:6][C:5]2=1.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:2]2[CH:3]=[C:4]3[C:12](=[C:13]([C:15]([NH2:17])=[O:16])[CH:14]=2)[NH:11][C:10]2[CH2:9][CH2:8][CH:7]([C:18]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[O:19])[CH2:6][C:5]3=2)=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A suspension of 6-bromo-3-(morpholine-4-carbonyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (50 mg, 0.123 mmol), 4-methoxyphenylboronic acid (37.4 mg, 0.246 mmol), K2CO3 (42.5 mg, 0.308 mmol), and PdCl2(dppf)-CH2C12 adduct (10.05 mg, 0.012 mmol) in dioxane (3 mL) was sealed in a microwave vial and it was heated in an oil-bath at 120° C. for 16 h. The reaction mixture was concentrated and the crude was purified by preparative HPLC to give 18 mg of 6-(4-methoxyphenyl)-3-(morpholine-4-carbonyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide as light brown solid. MS (ESI) m/z 434.2 (M+H). 1H NMR (methanol-d4) d ppm 7.64-7.73 (m, 2H) 7.52 (d, J=8.8 Hz, 2H) 6.89 (d, J=8.8 Hz, 2H) 3.73 (s, 3H) 3.52-3.67 (m, 8H) 3.00-3.12 (m, 1H) 2.70-2.89 (m, 4H) 1.83-2.09 (m, 2H).

Workup

customwas sealed in a microwave vial and it
concentrationThe reaction mixture was concentrated
customthe crude was purified by preparative HPLC

Sources & evidence

ORD record: ord-922055bdeb6e441a8ec7d4e79a34c246
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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