Water → HCID 86616298, compound

HRID 425166Notes

Reaction equation

HRID 425166 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][N:9](CC1C=CC(OC)=CC=1OC)[CH2:8]2)=[O:4].[C:25]1(OC)C=CC=CC=1.O.C(Cl)Cl.[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]>>[F:40][C:39]([F:42])([F:41])[C:37]([OH:43])=[O:38].[CH2:1]([O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][NH:9][CH2:8]2)=[O:4])[CH3:25]

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 59007009HCID 59007009, compound

Product 1

HCID 86616298HCID 86616298, compound

Procedure

A solution of 2-(2,4-dimethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid methyl ester (215 mg) and anisole (200 μl) in 1 ml of TFA was heated at 140° C. for 30 minutes in a CEM discover microwave synthesiser. The reaction was partititioned between water and DCM, the water layer was separated, washed with DCM then evaporated and re-evaporated with toluene/MeOH (×2) to give 105 mg of the title compound. 1H NMR (DMSO-d6) 9.70 (2H, br s), 8.02 (1H, s), 8.98 (1H, d), 7.57 (1H, d), 4.60 (2H, s), 4.56 (2H, s), 3.89 (3H, s).

Workup

  1. customthe water layer was separated
  2. washwashed with DCM
  3. customthen evaporated
  4. customre-evaporated with toluene/MeOH (×2)

Sources & evidence

ORD record
ord-6d652ea993db422788746d53764ab51e
Source dataset
uspto-grants-2012_01
Patent number
US08106057B2

Reaction notes

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