Tetrabutylammonium Fluoride → HCID 57501776, compound

HRID 601542Notes

Reaction equation

HRID 601542 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:36])[N:12]([C:17]4[CH:18]=[C:19]5[C:23](=[CH:24][CH:25]=4)[N:22]([Si](C(C)C)(C(C)C)C(C)C)[CH:21]=[CH:20]5)[CH2:13][CH2:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:36])[N:12]([C:17]4[CH:18]=[C:19]5[C:23](=[CH:24][CH:25]=4)[NH:22][CH:21]=[CH:20]5)[CH2:13][CH2:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57501775HCID 57501775, compound

Product 1

HCID 57501776HCID 57501776, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Mix 2-(4-chloro-phenyl)-5-(1-triisopropylsilanyl-1H-indol-5-yl)-6,7-dihydro-5H-thiazolo[5,4-c]pyridin-4-one (4.23 g, 7.89 mmol) in THF (50 mL) and add tetrabutyl-ammonium fluoride (1.0M in THF, 10 vmL, 10 mmol). Stir the red solution at room temperature for 2 h, then quench with aqueous 2M NH4Cl (50 mL) and extract with CH2Cl2 (3×50 mL). Dry, filter, and concentrate the organic solution. Purify the crude material by flash chromatography, using 8% MeOH (2N NH3)/CHCl3 as eluent, then triturate the resulting yellow solid with ether to give the title compound (2.68 g, 89%). MS (ES+) 380.0 (M+1)+. 1H NMR (400 MHz, CDCl3): δ 11.20 (s, 1H), 8.05 (d, 2H, J=8.4 Hz), 7.62 (d, 2H, J=8.4 Hz), 7.53 (d, 1H, J=1.8 Hz), 7.43-7.38 (m, 2H), 7.09 (dd, 1H, J=8.6, 2.0 Hz), 6.45-6.43 (m, 1H), 4.11 (t, 2H, J=7.0 Hz), 3.28 (t, 2H, J=7.0 Hz).

Workup

  1. customquench with aqueous 2M NH4Cl (50 mL)
  2. extractionextract with CH2Cl2 (3×50 mL)
  3. customDry
  4. filtrationfilter
  5. concentrationconcentrate the organic solution
  6. customPurify the crude material by flash chromatography
  7. customtriturate the resulting yellow solid with ether

Sources & evidence

ORD record
ord-55ba4e0dba0c4bdabeb69564b1b71663
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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