Dimethylformamide → HCID 58930429, compound

HRID 852940Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:22]1([NH2:29])[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH2:28].CCN(CC)CC.CN([CH:40]=[O:41])C>CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[NH2:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[NH:29][C:40](=[O:41])[C:18]1[CH:19]=[CH:20][C:15]([S:12](=[O:14])(=[O:13])[NH:11][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 223 (705 mg, 1.7 mmol), 1,2-phenylenediamine (199 mg, 1.84 mmol), Pd(OAc)2 (0.25 mmol, 15%) and 1,1′-bis(diphenylphosphino) ferrocene (160 mg, 0.29 mmol) was suspended in degassed DMF (10 mL), treated with Et3N (700 μL, 5.04 mmol), heated under CO atmosphere (balloon) for 18 h at 70° C. After evaporation of the DMF in vacuo, the residue was purified by flash chromatography (eluent AcOEt:hexane, 3:1) to give the title compound 224 (100 mg, 14% yield). 1H-NMR (CD3OD-d4), δ (ppm): 10.05 (s, 1H), 9.76 (s, 1H), 8.06 (d, J=8.3 Hz, 2H), 7.79 (d, J=7.8 Hz, 2H), 7.11 (bs, 1H), 6.94 (bs, 1H), 6.77-6.69 (m, 3H), 6.54 (bs, 2H), 4.91 (bs, 2H), 3.62 (s, 3H).

Workup

customAfter evaporation of the DMF in vacuo
customthe residue was purified by flash chromatography (eluent AcOEt:hexane, 3:1)

Sources & evidence

ORD record: ord-42e72a01374a4b25a870c31efb98a816
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253204B2

Reaction notes

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