Pyridine → HCID 59596278, compound

HRID 2264711Notes

Reaction equation

HRID 2264711 reaction equation
FC(F)(F)[C:3]([OH:5])=[O:4].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3([C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=4)[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:24]([NH2:31])=[N:23]3)[CH:17]=2)[CH:13]=[CH:14][CH:15]=1.N1[CH:45]=[CH:44][CH:43]=CC=1.[F:46][C:47]([F:60])([F:59])[S:48]([O:51]S(C(F)(F)F)(=O)=O)(=[O:50])=[O:49].Cl[CH2:62]Cl>>[C:44]([O:5][C:3]([NH:31][C:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]([C:18]2[CH:19]=[CH:20][C:21]([O:51][S:48]([C:47]([F:60])([F:59])[F:46])(=[O:49])=[O:50])=[C:16]([C:12]3[CH:13]=[CH:14][CH:15]=[C:10]([O:9][CH3:8])[CH:11]=3)[CH:17]=2)([C:32]2[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=2)[N:23]=1)=[O:4])([CH3:43])([CH3:45])[CH3:62]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 67749Trifluoromethanesulfonic anhydrideHCID 24874900HCID 24874900, compound

Product 1

HCID 59596278HCID 59596278, compoundYield 93%

Procedure

To [3-(6-hydroxy-3′-methoxy-biphenyl-3-yl)-3-(4-methoxy-phenyl)-3H-isoindol-1-yl]-carbamic acid tert-butyl ester (Scheme #2, F) (196 mg, 0.365 mmol) in an ice cold solution of dichloromethane was added pyridine (60.0 uL, 0.730 mmol) followed by trifluoromethanesulfonic anhydride (93 uL, 0.438 mmol). After stirring for 30 minutes the reaction was removed of solvent under reduced pressure and the crude mixture was purified on 20 g silica eluting with 5% acetone/dichloromethane to give the title compounds as a white solid (226 mg, 93%). 1H NMR (300 MHz, DMSO-d6) δ 7.86 (d, J=7.5 Hz, 1 H), 7.72-7.64 (m, 2 H), 7.58-7.36 (m, 5 H), 7.28-7.20 (m, 2 H), 7.02-6.84 (m, 5 H), 3.77 (s, 3 H), 3.72 (m, 3 H), 1.49 (m, 9 H); MS (APCI+) m/z 669 [M+1]+; tR=2.94 min.

Workup

  1. customwas removed of solvent under reduced pressure
  2. customthe crude mixture was purified on 20 g silica eluting with 5% acetone/dichloromethane

Sources & evidence

ORD record
ord-62dcddcbd0ca44f9b22340a7c3226e32
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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