Potassium Carbonate → tert-Butyl 2-nitro-4-(thiophen-2-yl)phenylcarbamate

HRID 1907689Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.Br[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[C:12]([N+:24]([O-:26])=[O:25])[CH:11]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.CCOC(C)=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>[N+:24]([C:12]1[CH:11]=[C:10]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[CH:15]=[CH:14][C:13]=1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])([O-:26])=[O:25]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 2-thiophene boronic acid (3.93 g, 30.7 mmol), bromoarene 2 (7.31 g, 23.1 mmol), tri-o-tolyl-phosphine (2.16 g, 7.1 mmol) and potassium carbonate (9.81 g, 70.9 mmol) in degassed ethyleneglycol dimethylether (DME) (120 mL) and H2O (40 mL) was treated with tetrakis(triphenylphosphine)palladium(0) (1.78 g, 1.5 mmol). The mixture was stirred in a preheated oil bath at 80° C. for 18 h, diluted with AcOEt (200 mL), washed with brine, dried over MgSO4 and concentrated. The crude material was either purified by flash chromatography (eluent: 10% AcOEt in hexane) or triturated in a mixture AcOEt:hexane (10:1, 100 mL) to give title compound 3 (6.74 g, 90% yield).

Workup

washwashed with brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe crude material was either purified by flash chromatography (eluent: 10% AcOEt in hexane)
customtriturated in a mixture AcOEt:hexane (10:1, 100 mL)

Sources & evidence

ORD record: ord-e8f6b729bb504a55b1e659aa1edfc160
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598168B2

Reaction notes

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