Sodium Carbonate → 2-Nitro-4-(thiophen-2-yl)aniline

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	4-Bromobenzene-1,2-diamine	HCID 323593	—
Reactant	2-Thiopheneboronic acid	HCID 2733960	—
Reactant	N,N-Dimethylformamide--water (1/1)	HCID 21962138	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-Nitro-4-(thiophen-2-yl)aniline	HCID 22664831	—

Reaction Conditions

Temperature	23 °C

Reaction Steps

4-Bromobenzene-1,2-diamine (1.0 equivalent) and Na2CO3 (2.0 equivalents) were dissolved in DMF/H2O (5:1) at room temperature. Nitrogen was bubbled through the reaction mixture for 5 minutes and PdCl2(dppf)2 (0.1 equivalents) was added. After stirring at 23° C. for approximately 10 minutes, 2-thiopheneboronic acid (1.1 equivalents) in DMF was added and the reaction was heated at 90° C. for 12 hours. After this time, the solution was concentrated and partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The resulting black residue was purified by silica gel chromatography (0-20% EtOAc:hexanes) to yield an orange solid. LC/MS m/z 221.1 (MH+), Rt 2.67 minutes.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07470709B2
Source dataset	uspto-grants-2008_12
ORD ID	ord-0c75f56832b1437abb34e939f1d8af2b
Source note	uspto-grants-2008_12