Dimethylformamide → HCID 178509773, compound

HRID 549480Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:24](=[CH:25][CH:26]=1)[C:12]1[NH:13][C:14]([C:16]3[C:21](Br)=[CH:20][CH:19]=[CH:18][C:17]=3Br)=[N:15][C:11]=1[C:10]1[CH:9]=[CH:8][C:7]([Cl:27])=[CH:6][C:5]2=1.[C:28]([Cu])#[N:29].[CH3:31][N:32](C=O)C>[Cl-].[Na+].O.C(OCC)(=O)C>[Br:1][C:2]1[CH:26]=[C:25]2[C:24](=[CH:4][CH:3]=1)[C:12]1[NH:13][C:14]([C:16]3[C:17]([C:28]#[N:29])=[CH:18][CH:19]=[CH:20][C:21]=3[C:31]#[N:32])=[N:15][C:11]=1[C:10]1[CH:5]=[CH:6][C:7]([Cl:27])=[CH:8][C:9]2=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 26 g of 9-bromo-6-chloro-2-(2,6-dibromophenyl)-11H-phenanthro[9,10-d]imidazole from Step 4 in 200 mL of dry DMF, was added 14.2 g of CuCN. The reaction was stirred overnight at 85° C., cooled down to room temperature, brine was added and the mixture stirred for 30 minutes. The solution was diluted in ethyl acetate, washed with 10% ammonium hydroxide, brine, dried over sodium sulphate and volatiles were removed under reduced pressure to afford 26 g of 2-(9-bromo-6-chloro-1H-phenanthro[9,10-d]imidazol-2-yl)isophthalonitrile as a solid. 1H NMR (Acetone-d6): 9.19 (s, 1H), 9.02 (s, 1H), 9.71 (bs, 1H), 8.49 (bs, 1H), 8.39 (d, 2H), 8.07 (t, 1H), 7.97 (d, 1H), 8.81 (d, 1H).

Workup

temperaturecooled down to room temperature
stirringthe mixture stirred for 30 minutes
washwashed with 10% ammonium hydroxide, brine
dry with materialdried over sodium sulphate and volatiles
customwere removed under reduced pressure

Sources & evidence

ORD record: ord-eb27acc9674d4a2e83b0b010f792a33b
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943649B2

Reaction notes

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