Tetrabutylammonium Fluoride → HCID 136400775, compound

HRID 876392Notes

Reaction equation

HRID 876392 reaction equation
[Si]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([C:19]1[N:23]3[CH:24]=[CH:25][C:26]([CH2:28][N:29]4[C:37](=[O:38])[C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[C:30]4=[O:39])=[CH:27][C:22]3=[N:21][N:20]=1)[CH:15]=[CH:14]2)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([C:19]1[N:23]3[CH:24]=[CH:25][C:26]([CH2:28][N:29]4[C:37](=[O:38])[C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[C:30]4=[O:39])=[CH:27][C:22]3=[N:21][N:20]=1)[CH:15]=[CH:14]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67231570HCID 67231570, compound

Product 1

HCID 136400775HCID 136400775, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-((3-(8-(tert-butyldimethylsilyloxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)methyl)isoindoline-1,3-dione (1.012 g, 1.889 mmol) and silica gel (3 g) in THF (20 mL) was added TBAF (2.267 mL, 2.267 mmol) (1M in THF). The reaction was stirred for 20 minutes, then filtered and washed with DCM/MeOH (10:1). The combined organics were concentrated in vacuo to afford the desired crude product.

Workup

  1. filtrationfiltered
  2. washwashed with DCM/MeOH (10:1)
  3. concentrationThe combined organics were concentrated in vacuo

Sources & evidence

ORD record
ord-74d1900dcc0745ac923936e1e593e5ef
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

Loading…