Dimethylformamide → 8-Cyanonaphthalene-2-sulfonamide

HRID 528794Notes

Reaction equation

I[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([S:12]([NH2:15])(=[O:14])=[O:13])[CH:8]=[CH:7]2.[CH3:16][N:17](C=O)C>[Li+].[Cl-].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>[C:16]([C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([S:12]([NH2:15])(=[O:14])=[O:13])[CH:8]=[CH:7]2)#[N:17]

Participants

Conditions

Temperature: 125 °C

Procedure

A solution of 8-iodonaphthalene-2-sulfonamide (Intermediate 7, 100 mg, 0.30 mmol), ZnCN (11 μL, 0.180 mmol) and Pd(PPh3)4 (14 mg, 0.012 mmol) in DMF (1.5 mL) was purged with argon for 5 min. The reaction mixture was then heated to 125° C. in a microwave reactor for 30 min. Additional ZnCN (33 μL, 0.54 mmol) and Pd(PPh3)4 (280 mg, 0.24 mmol) were added, and the reaction mixture was heated at 125° C. for 12 h. The reaction mixture was cooled to room temperature, diluted with 10% aq. LiCl solution and extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (22 mg, 30%). 1H NMR (CD3OD) δ 8.77 (d, J=0.9 Hz, 1H), 8.35 (d, J=8.4 Hz, 1H), 8.25 (d, J=8.8 Hz, 1H), 8.19 (d, J=7.3 Hz, 1H), 8.14 (d, J=1.8 Hz, 1H), 7.85-7.75 (m, 1H); MS(ESI+) m/z 250.1 (M+NH4)+.

Workup

temperaturethe reaction mixture was heated at 125° C. for 12 h
temperatureThe reaction mixture was cooled to room temperature
extractionextracted with EtOAc (3×)
dry with materialThe combined organic extracts were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-8cd24e67be5d450088fc6fc736c9e6ac
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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