Imidazole → HCID 68583228, compound

HRID 13718Notes

Reaction equation

HRID 13718 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[F:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[C:33]([C:41]1[C:49]3[C:44](=[C:45]([NH:50][S:51]([CH3:54])(=[O:53])=[O:52])[CH:46]=[CH:47][CH:48]=3)[NH:43][CH:42]=1)([CH2:37][CH2:38][CH2:39]O)[CH2:32][CH2:31]2>O1CCCC1.CCOCC>[F:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[C:33]([C:41]1[C:49]3[C:44](=[C:45]([NH:50][S:51]([CH3:54])(=[O:53])=[O:52])[CH:46]=[CH:47][CH:48]=3)[NH:43][CH:42]=1)([CH2:37][CH2:38][CH2:39][I:25])[CH2:32][CH2:31]2

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 58941680HCID 58941680, compound

Product 1

HCID 68583228HCID 68583228, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triphenylphosphine (422 mg, 1.61 min ol, 1.30 equivalents) and imidazole (219 mg, 3.22 mmol, 2.60 equivalents) in anhydrous tetrahydrofuran (10 ml) add iodine (410 mg, 1.61 mmol, 1.30 equivalents). After stirring for 20 minutes at room temperature under nitrogen, add N-{3-[5-Fluoro-1-(3-hydroxy-propyl)-indan-1-yl]-1H-indol-7-yl}-methanesulfonamide (500 mg, 1.24 mmol) and stir for 48 hours. Dilute with ether, wash with water (2×), wash with 1N aqueous hydrochloric acid (2×), dry over anhydrous sodium sulfate, filter, and concentrate the solution. Purify the residue on silica eluting with 50 to 100% ethyl acetate/hexanes over 25 minutes to obtain the title compound as a white solid (254 mg, 40%). LC-MS m/z 385.0 (M+−I).

Workup

  1. stirringstir for 48 hours
  2. washwash with water (2×)
  3. washwash with 1N aqueous hydrochloric acid (2×)
  4. dry with materialdry over anhydrous sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate the solution
  7. customPurify the residue on silica eluting with 50 to 100% ethyl acetate/hexanes over 25 minutes

Sources & evidence

ORD record
ord-c7481052f6bc42e8971ee286f015d7e4
Source dataset
uspto-grants-2010_06
Patent number
US07728150B2

Reaction notes

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