Triethylsilane → 6-Methoxy-5-methylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 1965469Notes

Reaction equation

HRID 1965469 reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3([C:20]4[CH:21]=[C:22]([CH3:27])[C:23]([O:25][CH3:26])=[CH:24][C:19]=4[O:18][CH2:17]3)[C:9]2=[O:28])C=CC=CC=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH3:26][O:25][C:23]1[C:22]([CH3:27])=[CH:21][C:20]2[C:10]3([CH2:17][O:18][C:19]=2[CH:24]=1)[C:11]1[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:8][C:9]3=[O:28]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 593524081'-(diphenylmethyl)-6-methoxy-5-methylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

Product 1

HCID 593522256-Methoxy-5-methylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneYield 86.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A stirred solution of 1′-(diphenylmethyl)-6-methoxy-5-methylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (7.2 g, 16.1 mmol), triethylsilane (15 mL) and trifluoroacetic acid (50 mL) was refluxed for 14 h. The solution was concentrated in vacuo and precipitated from hexanes to afford 6-methoxy-5-methylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (3.9 g, 86%) as a colorless solid: mp>250° C.; 1H NMR (300 MHz, DMSO-d6) δ10.54 (s, 1H), 7.23-7.14 (m, 1H), 7.03 (d, J=6.9 Hz, 1H), 6.95-6.86 (m, 2H), 6.58 (s, 1H), 6.41 (s, 1H), 4.68 (ABq, 2H), 3.73 (s, 3H), 1.91 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ179.2, 160.4, 158.9, 142.2, 133.4, 129.1, 124.4, 124.2, 122.7, 120.3, 118.5, 110.2, 94.3, 80.1, 58.0, 56.0, 16.0; MS (ES+) m/z 282.2 (M+1).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customprecipitated from hexanes

Sources & evidence

ORD record
ord-17dbd8e9d0eb4d5ab48915259fb2b343
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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