Pyridine → HCID 59596285, compound

HRID 2264723Notes

Reaction equation

HRID 2264723 reaction equation
FC(F)(F)[C:3]([OH:5])=[O:4].[NH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:25]2[CH:30]=[CH:29][C:28]([O:31][S:32]([CH3:35])(=[O:34])=[O:33])=[CH:27][CH:26]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[CH:19]=2)[N:10]=1.N1[CH:41]=[CH:40][CH:39]=CC=1.[CH3:42]S(Cl)(=O)=O>O1CCCC1>[Br:24][C:20]1[CH:19]=[C:18]([C:11]2([C:25]3[CH:30]=[CH:29][C:28]([O:31][S:32]([CH3:35])(=[O:34])=[O:33])=[CH:27][CH:26]=3)[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]([NH:8][C:3]([O:5][C:40]([CH3:39])([CH3:41])[CH3:42])=[O:4])=[N:10]2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 31297Methanesulfonyl chloride2×HCID 24875148HCID 24875148, compound

Product 1

HCID 59596285HCID 59596285, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To [3-(3-bromo-phenyl)-3-(4-hydroxy-phenyl)-3H-isoindol-1-yl]-carbamic acid tert-butyl ester (Scheme #6, S) (900 mg, 1.88 mmol) in tetrahydrofuran (10 mL) was added pyridine (306 uL, 3.76 mmol) and methanesulfonyl chloride (218 uL, 2.82 mmol). After stirring over night, additional pyridine (306 uL, 3.76 mmol) and methanesulfonyl chloride (218 uL, 2.82 mmol) were added and the reaction allowed to stir for 8 hours. The solvent was removed under reduced pressure and the resulting oil put under high vacuum. The crude material was chromatographed on 20 g silica gel eluting with 2.5% methanol/dichloromethane and the combined purified fractions removed of solvent to give the title compound as a white solid (734 mg, 70%). 1H NMR (500 MHz, DMSO-d6/TFA-d) δ 8.67 (d, J=8.0 Hz, 1 H), 7.92 (t, J=7.6 Hz, 1 H), 7.84 (d, J=7.8 Hz, 1 H), 7.78 (t, J=7.7 Hz, 1 H), 7.62 (d, J=7.6 Hz, 2 H), 7.49 (d, J=8.7 Hz, 2 H), 7.39-7.33 (m, 4 H), 3.40 (s, 3 H), 1.63 (s, 9 H); MS (ES+) m/z 557 [M+1]+; tR=2.29 min.

Workup

  1. stirringto stir for 8 hours
  2. customThe solvent was removed under reduced pressure
  3. customThe crude material was chromatographed on 20 g silica gel eluting with 2.5% methanol/dichloromethane
  4. customthe combined purified fractions
  5. customremoved of solvent

Sources & evidence

ORD record
ord-efbed3fb42b14ebe82c29f5cffb1a6f5
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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