1-Hydroxybenzotriazole → (5-Bromo-2,4-Dihydroxyphenyl)(1,3-Dihydro-2h-Isoindol-2-Yl)methanone

HRID 2412195Notes

Reaction equation

HRID 2412195 reaction equation
[Br:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.Cl.CN(C)CCCN=C=NCC.C1C=CC2N(O)N=NC=2C=1.[CH2:35]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:37][NH:36]1>CN(C=O)C>[Br:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]([OH:11])=[C:6]([C:7]([N:36]2[CH2:37][C:38]3[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:35]2)=[O:9])[CH:10]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 818145-Bromo-2,4-dihydroxybenzoic acidHCID 422478IsoindolineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 15942234(5-Bromo-2,4-Dihydroxyphenyl)(1,3-Dihydro-2h-Isoindol-2-Yl)methanoneYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromo-2,4-dihydroxy-benzoic acid (520 mg, 2.33 mmol) in DMF (5 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (471 mg, 2.45 mmol) then HOBt (362 mg, 2.68 mmol). After 25 min, 2,3-dihydro-1H-isoindole (0.5 mL, 2.63 mmol) was added then the mixture was stirred at r.t. for 18 h. The solvent was removed in vacuo then the residue was taken up in ethyl acetate and washed with 1N hydrochloric acid, saturated sodium bicarbonate solution and brine then dried (MgSO4) and concentrated. The residue was triturated with methanol to afford the title compound as a grey solid (328 mg, 44%). 1H NMR (DMSO-d6) 10.45 (1H, s), 10.32 (1H, s), 7.36 (1H, br.s), 7.35 (1H, s), 7.28 (3H, br.s), 6.59 (1H, s), 4.77 (2H, br.s), 4.71 (2H, br.s). MS: [M+H]+ 332/334.

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed with 1N hydrochloric acid, saturated sodium bicarbonate solution and brine
  3. dry with materialthen dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was triturated with methanol

Sources & evidence

ORD record
ord-12099ede34524c22be5b108ca9a8d445
Source dataset
uspto-grants-2014_08
Patent number
US08816087B2

Reaction notes

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