Benzo(B)Thiophene-2-Boronic Acid → HCID 10202383, compound

HRID 1829810Notes

Reaction equation

HRID 1829810 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[O:5][CH2:6][CH2:7][C@@H:8]([N:12]1[CH:16]=[C:15]([C:17]([NH2:19])=[O:18])[N:14]=[CH:13]1)[C@@H:9]([OH:11])[CH3:10].[S:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[CH:25]=[C:24]1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[S:23]1[C:24]([C:2]2[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=2)[O:5][CH2:6][CH2:7][C@@H:8]([N:12]2[CH:16]=[C:15]([C:17]([NH2:19])=[O:18])[N:14]=[CH:13]2)[C@@H:9]([OH:11])[CH3:10])=[CH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]1=2

Participants

7

Reactant 3

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 10340Sodium CarbonateHCID 10177039HCID 10177039, compound

Product 1

HCID 10202383HCID 10202383, compoundYield 62.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 1-[(2S,3R)-5-(3-bromophenoxy)-2-hydroxy-3-pentyl]imidazole-4-carboxamide in DME (5 ml) was added Pd(PPh3)4 (29.3 mg, 0.025 mmol)at ambient temperature under N2. After stirring for 20 min., benzothiophene-2-boronic acid (54.2 mg, 0.304 mmol) and a solution of Na2CO3 (40.3 mg, 0.38 mmol) in H2O (1 ml) were added and the mixture was refluxed for 3 h. The mixture was cooled to room temperature and partitioned between ethyl acetate (20 ml) and H2O. The organic layer was washed successively with saturated NaHCO3 aqueous solution, H2O and then brine, dried (sodium sulfate) and evaporated in vacuo. The residue was purified by silica gel chromatography eluting with chloroform/methanol (100:1 to 20:1) to give 1-{(2S,3R)-5-[3-(2-benzo[b]thiophenyl)phenoxy]-2-hydroxy-3-pentyl}imidazole-4-carboxamide (41) (66.9 mg, 62.6%).

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. custompartitioned between ethyl acetate (20 ml) and H2O
  3. washThe organic layer was washed successively with saturated NaHCO3 aqueous solution, H2O
  4. dry with materialbrine, dried (sodium sulfate)
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with chloroform/methanol (100:1 to 20:1)

Sources & evidence

ORD record
ord-d2c0ec3594f2413b9dd1afa5aba187f0
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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