Dimethylformamide → HCID 16123108, compound

HRID 1642510Notes

Reaction equation

Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]1[CH:14]=[CH:13][CH:12]=[N:11][C:5]=1[NH:6]2.[C:15]1([SH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:22](=O)([O-])[O-].[Cs+].[Cs+].C[N:29]([CH:31]=[O:32])C>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]>[N:11]1[C:5]2[NH:6][C:7]3[C:3]([C:4]=2[CH:14]=[CH:13][CH:12]=1)=[C:2]([S:21][C:15]1[CH:20]=[CH:19][C:18]([NH:29][C:31](=[O:32])[CH3:22])=[CH:17][CH:16]=1)[CH:10]=[CH:9][CH:8]=3

Participants

Conditions

Temperature: 170 °C

Procedure

The title compound was synthesized by mixing Compound 4 (25 mg, 0.10 mmol, benzenethiol (21 μl, 0.20 mmol), caesium carbonate (33 mg, 0.10 mmol) and [1,1′-Bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (7 mg, 0.01 mmol) in DMF and heating at 170° C. for 20 minutes in a microwave reactor. The product was purified by HPLC (Yield=42%). 1H NMR (400 MHz, CH3OD) δ 8.97 (d, J=7.84 1 H) 8.41 (d, J=5.56 Hz 1 H) 7.55 (m, 3 H) 7.50 (t, 1 H) 7.40 (q, 1 H) 7.36 (d, J=8.84 Hz 2 H) 7.12 (d, J=7.36 Hz 1 H) 2.11 (s, 3 H). [M+H] calc'd for C19H15N3OS 334; found, 334.

Workup

customThe product was purified by HPLC (Yield=42%)

Sources & evidence

ORD record: ord-5e31a76e59df48cf95ad44bd6a5a6630
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119655B2

Reaction notes

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