Acetonitrile → HCID 86669785, compound

HRID 2371261Notes

Reaction equation

HRID 2371261 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:27](=[O:36])[NH:28][C:29]2[CH:34]=[CH:33][C:32](I)=[CH:31][CH:30]=2)[CH2:12][C:13]2[S:17][C:16]([C:18]([NH:20][CH2:21][CH2:22][S:23]([OH:26])(=[O:25])=[O:24])=[O:19])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[O:37]1[C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[CH:39]=[C:38]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(#N)C>COCCOC.C(O)C.O.CC1C=CC=CC=1[P](C1C=CC=CC=1C)([Pd](Cl)(Cl)[P](C1=C(C)C=CC=C1)(C1C=CC=CC=1C)C1C=CC=CC=1C)C1C=CC=CC=1C>[O:37]1[C:38]2=[CH:39][CH:40]=[CH:45][C:44]2=[CH:43][CH:42]=[C:41]1[N:28]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:27]([CH:11]([C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])=[CH:6][CH:7]=1)[CH2:12][C:13]1[S:17][C:16]([C:18]([NH:20][CH2:21][CH2:22][S:23]([OH:26])(=[O:25])=[O:24])=[O:19])=[CH:15][CH:14]=1)=[O:36]

Participants

9

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 86669786HCID 86669786, compound

Product 1

HCID 86669785HCID 86669785, compoundYield 12%

Reagents, catalysts & solvents 4

HCID 178424406HCID 178424406, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
125 °C

Procedure

To 2-({5-[2-(4-tert-Butyl-phenyl)-2-(4-iodo-phenylcarbamoyl)-ethyl]-thiophene-2-carbonyl}-amino)-ethanesulfonic acid (100 mg, 0.16 mmol) in 2 ml 1,2-dimethoxyethane, 1 ml ethanol, and 0.5 ml water was added benzofuran-2-boronic acid (76 mg, 0.47 mmol), sodium carbonate (83 mg, 0.78 mmol), and dichlorobis(tri-o-tolylphosphine)palladium(II) (12 mg, 0.016 mmol). The resulting mixture was heated to 125° C. in microwave for 6 minutes. Chromatography of the reaction mixture (20% to 80% acetonitrile in water) obtained 2-({5-[2-(4-Benzofuran-2-yl-phenylcarbamoyl)-2-(4-tert-butyl-phenyl)-ethyl]-thiophene-2-carbonyl}-amino)-ethanesulfonic acid as a white solid (12 mg, 12%).

Sources & evidence

ORD record
ord-83d4a1a47edd4d629e9cd3b540718015
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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