2,3-Dihydro-1-benzofuran-6-ol → 7-chloro-1-(diphenylmethyl)-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-one

HRID 1407413Notes

Reaction equation

HRID 1407413 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.C([Mg]Cl)(C)C.[Cl:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:25]=1[N:24]([CH:26]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:23](=[O:39])[C:22]2=[O:40]>O1CCCC1>[Cl:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:25]=1[N:24]([CH:26]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:23](=[O:39])[C:22]2([OH:40])[C:8]1[C:7]([OH:10])=[CH:6][C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=1

Participants

5

Reactant 3

HCID 122365402,3-Dihydro-1-benzofuran-6-olHCID 673566457-chloro-1-(diphenylmethyl)-1H-indole-2,3-dioneHCID 178418918HCID 178418918, compound

Product 1

HCID 673566647-chloro-1-(diphenylmethyl)-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-oneYield 387.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of 2,3-dihydrobenzofuran-6-ol (0.52 g, 3.8 mmol) in anhydrous tetrahydrofuran (25 mL) was added isopropylmagnesium chloride (2.1 mL, 2 M solution in tetrahydrofuran, 4.2 mmol). The resultant suspension was stirred at 0° C. for 0.5 h and followed by the addition of 7-chloro-1-(diphenylmethyl)-1H-indole-2,3-dione (2.11 g, 15.5 mmol) in one portion. The reaction mixture was stirred at ambient temperature for 3 h and concentrated in vacuo. The crude product was purified by column chromatography with ethyl acetate in hexanes (0% to 50% gradient) to afford 7-chloro-1-(diphenylmethyl)-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-one (7.12 g, 95%) as a colorless solid: 1H NMR (300 MHz, DMSO-d6) δ9.43 (s, 1H), 7.56-7.18 (m, 13H), 6.99-6.86 (m, 2H), 6.60 (s, 1H), 6.08 (s, 1H), 4.56 (t, J=8.6 Hz, 2H), 3.10 (t, J=8.6 Hz, 2H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude product was purified by column chromatography with ethyl acetate in hexanes (0% to 50% gradient)

Sources & evidence

ORD record
ord-41f488b17a5448fc958a45f930fdde8c
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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