1,2-Dichloroethane → (2,4-Bis-benzyloxy-5-isopropenyl-phenyl)-(5-bromo-1,3-dihydro-isoindol-2-yl)-methanone

HRID 1625370Notes

Reaction equation

HRID 1625370 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]([C:18]([CH3:20])=[CH2:19])=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[CH2:27][NH:26][CH2:25]2.C(Cl)CCl.[CH:35]1[CH:36]=[CH:37][C:38]2N(O)N=N[C:39]=2[CH:40]=1.CN([CH:48]=[O:49])C>>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:49][CH2:48][C:39]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:40]=2)[C:15]([C:18]([CH3:20])=[CH2:19])=[CH:14][C:10]=1[C:11]([N:26]1[CH2:25][C:24]2[C:28](=[CH:29][CH:30]=[C:22]([Br:21])[CH:23]=2)[CH2:27]1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 147958715-BromoisoindolineHCID 66672430Benzyloxy-5-isopropenyl-benzoic acid

Product 1

HCID 46915776(2,4-Bis-benzyloxy-5-isopropenyl-phenyl)-(5-bromo-1,3-dihydro-isoindol-2-yl)-methanone

Procedure

A solution of benzyloxy-5-isopropenyl-benzoic acid (2.85 g; 7.6 mmol), 5-bromo-2,3-dihydro-1H-isoindole (1.5 g; 1 equiv.), EDC (1.75 g; 1.2 equiv.) and HOBt (1.25 g; 1.2 equiv.) in DMF (25 ml) was stirred at room temperature overnight then evaporated. The residue was dissolved in EtOAc, washed with 2M HCl then saturated NaHCO3, dried (MgSO4) and evaporated. Purification using a Biotage SP4 (40S, 40 ml/min) eluting with 1:4-1:3-1:2 EtOAc/P.E. gave 2.45 g of (2,4-bis-benzyloxy-5-isopropenyl-phenyl)-(5-bromo-1,3-dihydro-isoindol-2-yl)-methanone as a light brown solid.

Workup

  1. customthen evaporated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with 2M HCl
  4. dry with materialsaturated NaHCO3, dried (MgSO4)
  5. customevaporated
  6. customPurification
  7. washeluting with 1:4-1:3-1:2 EtOAc/P.E

Sources & evidence

ORD record
ord-76a6a679a07744f3aef82e9600964657
Source dataset
uspto-grants-2014_07
Patent number
US08779132B2

Reaction notes

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