Potassium trimethylsilanolate → HCID 71285150, compound

HRID 1481756Notes

Reaction equation

[CH2:1]([O:8][C:9]1[N:18]=[C:17]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24]([CH3:28])[CH:23]=[C:22]3[C:29]#[N:30])[C:16]([CH2:31][CH3:32])=[C:15]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:10]=1[C:11]([O:13]C)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)[O-].[K+]>C1COCC1>[CH2:1]([O:8][C:9]1[N:18]=[C:17]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24]([CH3:28])[CH:23]=[C:22]3[C:29]#[N:30])[C:16]([CH2:31][CH3:32])=[C:15]([O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:10]=1[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 2,4-bis(benzyloxy)-6-(3-cyano-1-methyl-1H-indol-5-yl)-5-ethylnicotinate (130 mg, 0.24 mmol) in THF (2.5 mL) was added potassium trimethylsilanolate (80 mg, 0.62 mmol, 2.6 eq) at room temperature. Then the reaction mixture was heated to 60° C. and stirred for 8 h. Upon completion of the reaction, the solvents were removed under reduced pressure. The reaction was acidified with 1N HCl (1 mL) and then the reaction mixture was extracted with CH2Cl2 (3×20 mL). The solvent was removed to give a crude product which was purified by flash column chromatography (0-15% EtOAc in CH2Cl2) to afford the title compound (99 mg, 78%).

Workup

customUpon completion of the reaction
customthe solvents were removed under reduced pressure
extractionthe reaction mixture was extracted with CH2Cl2 (3×20 mL)
customThe solvent was removed
customto give a crude product which
customwas purified by flash column chromatography (0-15% EtOAc in CH2Cl2)

Sources & evidence

ORD record: ord-ad12ac903b744cfb88c1e16d482016fd
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409905B2

Reaction notes

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