Triethylsilane → 6-[2-(dimethylamino)ethoxy]spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 422856Notes

Reaction equation

HRID 422856 reaction equation
[CH3:1][N:2]([CH3:37])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]2[C:12]3([CH2:35][O:36][C:8]=2[CH:7]=1)[C:20]1[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=1)[N:14](C(C1C=CC=CC=1)C1C=CC=CC=1)[C:13]3=[O:34].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH3:1][N:2]([CH3:37])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]2[C:12]3([CH2:35][O:36][C:8]=2[CH:7]=1)[C:20]1[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH:14][C:13]3=[O:34]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 452804526-[2-(dimethylamino)ethoxy]-1'-(diphenylmethyl)spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

Product 1

HCID 452801616-[2-(dimethylamino)ethoxy]spiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneYield 106.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 6-[2-(dimethylamino)ethoxy]-1′-(diphenylmethyl)spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (0.75 g, 1.5 mmol), triethylsilane (1.3 mL, 8.2 mmol) and trifluoroacetic acid (10 mL) was refluxed for 3 h. The mixture was concentrated under vacuum, and the residue was treated with diethyl ether/hexanes to afford 6-[2-(dimethylamino)ethoxy]spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (0.52 g, 99%) as a colorless solid: mp 95-97° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.58 (s, 1H), 7.21 (td, J=7.6, 1.3 Hz, 1H), 7.04 (d, J=6.4 Hz, 1H), 6.97-6.84 (m, 2H), 6.64-6.57 (m, 2H), 6.40 (dd, J=8.3, 2.3 Hz, 1H), 4.79 (d, J=9.3 Hz, 1H), 4.67 (d, J=9.3 Hz, 1H), 4.25 (t, J=4.7 Hz, 2H), 3.45 (t, J=4.7 Hz, 2H), 2.81 (s, 6H); 13C NMR (75 MHz, DMSO-d6) δ 178.9, 162.1, 159.5, 142.3, 133.1, 129.2, 124.2, 124.1, 122.8, 122.7, 110.3, 108.2, 97.5, 80.4, 62.9, 57.6, 55.7, 43.2; MS (ES+) m/z 325.2 (M+1).

Workup

  1. temperaturewas refluxed for 3 h
  2. concentrationThe mixture was concentrated under vacuum
  3. additionthe residue was treated with diethyl ether/hexanes

Sources & evidence

ORD record
ord-8741403f40b14c64956ece347d5b5307
Source dataset
uspto-grants-2012_01
Patent number
US08101647B2

Reaction notes

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