Sodium Carbonate → HCID 86699136, compound

HRID 1424228Notes

Reaction equation

Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[C:12](C1C=CC(B(O)O)=CC=1)#[N:13].C([O-])([O-])=O.[Na+].[Na+].[C:29]1(C)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CCO.O>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>[NH2:6][C:5]1([C:12]#[N:13])[CH:7]=[CH:8][C:2]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:3][CH:4]1[N+:9]([O-:11])=[O:10]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 4-bromo-2-nitroaniline (1.92 g, 8.85 mmol) and 4-cyanophenylboronic acid (1.3 g, 8.85 mmol) in toluene/EtOH/water (3/1/1.5, 40 mL) was degassed thoroughly before the addition of Na2CO3 (2.8 g, 26.55 mmol) and Pd(PPh3)4 (511 mg, 0.44 mmol). The reaction was heated to 100° C. for 5 hours. After cooling the reaction was filtered through celite, washing through with EtOAc (3×20 mL). The filtrate was washed with water (2×30 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 2-3% MeOH in DCM to afford the title compound as a yellow solid (1.8 g, 85%).

Workup

temperatureAfter cooling the reaction
filtrationwas filtered through celite
washwashing through with EtOAc (3×20 mL)
washThe filtrate was washed with water (2×30 mL)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified
washeluting with 2-3% MeOH in DCM

Sources & evidence

ORD record: ord-ac55236d47e94646ba3cfa9d696eab35
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927587B2

Reaction notes

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