Sodium Carbonate → 3-[3-(2-Imidazol-1-ylacetyl)phenyl]-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

HRID 659696Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8](=[O:15])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)[CH:5]=[CH:6][CH:7]=1.[CH2:16]([C:20]1[S:24][C:23]([S:25]([NH:28][C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:27])=[O:26])=[C:22](B(O)O)[CH:21]=1)[CH:17]([CH3:19])[CH3:18].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)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:10]1([CH2:9][C:8]([C:4]2[CH:3]=[C:2]([C:22]3[CH:21]=[C:20]([CH2:16][CH:17]([CH3:18])[CH3:19])[S:24][C:23]=3[S:25]([NH:28][C:29]([CH3:31])([CH3:30])[CH3:32])(=[O:27])=[O:26])[CH:7]=[CH:6][CH:5]=2)=[O:15])[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-(3-bromophenyl)-2-imidazol-1-ylethanone (102 mg, 0.385 mmol; see step (a)) in toluene (10 mL) and ethanol (1 mL) was added 5-isobutyl-2-(N-tert-butylaminosulfonyl)thiophene-3-boronic acid (209 mg, 0.654 mmol; see Example 1(c)), Pd(PPh3)4 (26.7 mg, 0.023 mmol) and Na2CO3 (769 μL, 1.54 mmol, 2.0 M aq), and the reaction mixture was stirred for 4 h at 80° C. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc. The combined organic phase was dried (over anhydrous MgSO4), concentrated in vacuo, and the residue was purified by flash chromatography using MeOH:CH2Cl2 (6:94) as eluent to give the sub-title compound as a colourless syrup in 95% yield (168 mg, 0.366 mmol).

Workup

extractionextracted with EtOAc
dry with materialThe combined organic phase was dried (over anhydrous MgSO4)
concentrationconcentrated in vacuo
customthe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-7bdfe7d756da44f8a2385d6132dd2bee
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08080571B2

Reaction notes

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