Sodium Carbonate → Methyl 4-(((benzyloxy)carbonyl)amino)-5-bromo-2-(4-chlorophenyl)thiophene-3-carboxylate

HRID 1918209Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:19]([O:21][CH3:22])=[O:20])=[C:14](Br)[S:15][C:16]=1[Br:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:19]([O:21][CH3:22])=[O:20])=[C:14]([C:27]2[CH:28]=[CH:29][C:24]([Cl:23])=[CH:25][CH:26]=2)[S:15][C:16]=1[Br:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Palladium tetrakis-triphenylphosphine (19.3 mg, 17 μmol) was added to a degassed solution of dibromide 4 (150 mg, 334 μmol) and 4-chlorophenylboronic acid 5 (54.8 mg, 350 μmol) in ethanol: water:toluene (2:1:1, 1.67 mL) and sodium carbonate (177 mg, 1.6 mmol). The resulting mixture was heated under N2 and stirred for 1 h at 80° C. The mixture was then cooled filtered through a 0.45 μm syringe filter and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-50% ethyl acetate in hexane) provided 6 (76.8 mg, 48%) as a solid: LRESIMS m/z 479.8 [M+H]+, calcd. for C20H16Br1Cl1N1O4S1 480.0.

Workup

temperatureThe resulting mixture was heated under N2
temperatureThe mixture was then cooled
filtrationfiltered through a 0.45 μm syringe
filtrationfilter
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e8961604397248f2bfe1dc7f4e834f9d
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618307B2

Reaction notes

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