Tetrabutylammonium Fluoride → HCID 57722778, compound

HRID 222299Notes

Reaction equation

HRID 222299 reaction equation
[Si]([O:8][CH:9]([C:11]1[CH:12]=[CH:13][C:14]2[CH:25]=[CH:24][C:18]3=[N:19][CH:20]=[C:21]([Cl:23])[CH:22]=[C:17]3[C:16](=[O:26])[C:15]=2[CH:27]=1)[CH3:10])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:23][C:21]1[CH:22]=[C:17]2[C:16](=[O:26])[C:15]3[CH:27]=[C:11]([CH:9]([OH:8])[CH3:10])[CH:12]=[CH:13][C:14]=3[CH:25]=[CH:24][C:18]2=[N:19][CH:20]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57722880HCID 57722880, compound

Product 1

HCID 57722778HCID 57722778, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-chloro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (20 mg, 0.05 mmol) was taken up in 1 mL of tetrahydrofuran. Tetrabutylammonium fluoride (0.06 mL of 1.0M in THF, 0.06 mmol) was added and the mixture was stirred at room temperature for 45 min. The reaction was concentrated in vacuo and directly purified via flash chromatography (silica, 0-35% ethyl acetate/hexanes) to afford the title compound. 1H NMR (600 MHz, CDCl3) δ 8.80 (d, 1H); 8.50 (d, 1H); 8.23 (d, 1H); 7.76 (dd, 1H); 7.60 (d, 1H); 7.31 (d, 1H); 7.26 (d, 1H); 5.06 (q, 1H); 1.55 (d, 3H). Hydroxyl proton was not observed. LRMS (APCI) calc'd for (C16H13ClNO2) [M+H]+, 286.1; found 286.1.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customdirectly purified via flash chromatography (silica, 0-35% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-787017ac41734e899abc804d82dfe95e
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

Loading…