Toluene → 3-(4-ethoxyphenyl)-7-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide

HRID 2410700Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:23]([NH2:25])=[O:24])[C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[C:9]([C:15]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:16])[CH:8]=3.[CH2:26]([O:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)[CH3:27].C([O-])([O-])=O.[Na+].[Na+].C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO>[CH2:26]([O:28][C:29]1[CH:34]=[CH:33][C:32]([C:2]2[CH:3]=[C:4]([C:23]([NH2:25])=[O:24])[C:5]3[NH:6][C:7]4[C:12]([C:13]=3[CH:14]=2)=[CH:11][CH:10]=[C:9]([C:15]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)=[O:16])[CH:8]=4)=[CH:31][CH:30]=1)[CH3:27]

Participants

Conditions

Temperature: 100 °C

Procedure

3-Bromo-7-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide (57 mg, 0.142 mmol), 4-ethoxyphenylboronic acid (35.3 mg, 0.213 mmol), Pd(Ph3P)4 (16.37 mg, 0.014 mmol) and aqueous Na2CO3 (2M) (0.177 mL, 0.354 mmol) were mixed with toluene (2 mL) and MeOH (1 mL) in a sealed microwave tube. The mixture was degassed and filled with N2. then stirred at 100° C. for 12 hrs. The reaction mixture was concentrated and purified using preparative HPLC to give 11.1 mg of titled product. MS (ESI) m/z 444.21 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.53 (s, 1H), 8.64 (s, 1H), 8.37 (bs, 1H), 8.29 (m, 2H), 7.81 (m, 3H), 7.56 (bs, 1H), 7.22 (d, 1H, J=8), 7.07(m, 2H), 4.10 (q, 2H, J=6.9), 3.64 (bm, 8H), 1.37 (t, 3H, J=6.9).

Workup

customThe mixture was degassed
additionfilled with N2
concentrationThe reaction mixture was concentrated
custompurified

Sources & evidence

ORD record: ord-df009149b55f492b8126396733e648d7
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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