Toluene → HCID 19430472, compound

HRID 1078040Notes

Reaction equation

HRID 1078040 reaction equation
[F:1][C:2]1[CH:18]=[C:17](I)[CH:16]=[CH:15][C:3]=1[CH2:4][N:5]1[CH:9]=[C:8]([CH2:10][CH3:11])[N:7]=[C:6]1[CH2:12][CH2:13][CH3:14].O(C1C=CC=C(C=1)CCC(CC[C:38]1[CH:43]=[C:42]([O:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:41]=[CH:40][CH:39]=1)=O)C1C=CC=CC=1.[C:52]([NH:56][S:57]([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=1B(O)O)(=[O:59])=[O:58])([CH3:55])([CH3:54])[CH3:53].[C:69](=[O:72])([O-])[O-].[C:73]1(C)C=CC=C[CH:74]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[C:52]([NH:56][S:57]([C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][C:61]=1[C:17]1[CH:16]=[CH:15][C:3]([CH2:4][N:5]2[C:9]([C:69]([CH2:73][CH2:74][C:50]3[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=3[O:44][C:42]3[CH:43]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[O:72])=[C:8]([CH2:10][CH3:11])[N:7]=[C:6]2[CH2:12][CH2:13][CH3:14])=[C:2]([F:1])[CH:18]=1)(=[O:59])=[O:58])([CH3:55])([CH3:54])[CH3:53]

Participants

7

Reactant 4

HCID 1140TolueneHCID 19660Carbonate IonHCID 4997616Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-HCID 70079048HCID 70079048, compound

Product 1

HCID 19430472HCID 19430472, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

1-(2-fluoro-4-iodobenzyl)-4-ethyl-2-propyl-1H-imidazole-5-phenoxyphenethyl ketone (2.35 g, 3.90 mmol), 2-(t-butylamino)sulfonylphenyl boronic acid (1.52 g, 5.85 mmol), and soduim carbonate (10 mL of 2M aqueous solution), and tetrabutylammonium bromide (65 mg, o.20 mmol) were added together with 50 mL of toluene. Tetrakis(triphenylphosphine) palladium(O) (0.23 g, 0.20 mmol) was added. The mixture was refluxed under N2 overnight. The solvent was removed in vacuo and the residue was partitioned between H2O and CH2Cl2. The aqueous layer was extracted with CH2Cl2, and the combined organic solution was washed with brine, dried over MgSO4 and concentrated. The crude product was purified by flash column chromatography (silica gel, 30% EtOAc/hexane) to give 1.92 g of light yellow foam (72%). MS m/e 682.5, [M+H]+ ; 1H NMR (300 MHz, CDCl3): δ 0.96 (t, 3H, CH3), 0.98 (t, 9H, CH3), 1.27 (t, 3H, CH3), 1.69 (m, 2H, CH2), 2.60 (t, 2H, CH2), 2.85 (q, 2H, CH2), 2.97 (m, 2H, CH2), 3.13 (m, 2H, CH2), 3.58 (s, 1H, NH), 5.57 (s, 2H, CH2Ar), 6.60 (t, 1H, ArH), 6.86 (d, 1H, ArH), 6.92 (d, 2H, ArH), 7.05 (d, 2H, ArH), 7.16 (m, 2H, ArH), 7.26 (m,5H, ArH), 7.55 (m, 2H, ArH), 8.16 (m, 1H, ArH). ##STR67##

Workup

  1. temperatureThe mixture was refluxed under N2 overnight
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between H2O and CH2Cl2
  4. extractionThe aqueous layer was extracted with CH2Cl2
  5. washthe combined organic solution was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe crude product was purified by flash column chromatography (silica gel, 30% EtOAc/hexane)

Sources & evidence

ORD record
ord-0242ba309be84d74bf036636d8703213
Source dataset
uspto-grants-1996_08
Patent number
US05545651

Reaction notes

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