Tetrabutylammonium Fluoride → HCID 58266499, compound

HRID 1888488Notes

Reaction equation

HRID 1888488 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:37]=[N:36][C:18]3[N:19](COCC[Si](C)(C)C)[C:20]4[CH:25]=[N:24][C:23]([C:26]#[N:27])=[CH:22][C:21]=4[C:17]=3[CH:16]=2)=[CH:11][CH:10]=1)[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[CH2:1]([N:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:37]=[N:36][C:18]3[NH:19][C:20]4[CH:25]=[N:24][C:23]([C:26]#[N:27])=[CH:22][C:21]=4[C:17]=3[CH:16]=2)=[CH:11][CH:10]=1)[CH3:2]

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58266844HCID 58266844, compound

Product 1

HCID 58266499HCID 58266499, compoundYield 20%

Procedure

A solution of 3-[4-(1-ethyl-piperidin-2-yl)-phenyl]-9-(2-trimethylsilanylethoxy methyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (75 mg, 0.147 mmol) in TBAF (1M in THF, 1.5 mL, 1.47 mmol) was heated at 55° C. for 16 h. The reaction mixture was concentrated in vacuo and the resultant residue was partitioned between water and ethyl acetate. The organic layer was separated, dried over sodium sulfate, filtered and evaporated to give a yellow solid. The resultant solid was purified by flash chromatography (silica, Biotage 50 g column, 0-100% (10% methanol in DCM)) to afford the title compound (11 mg, 20%). 1H NMR (DMSO-D6, 400 MHz): 12.89 (s, 1H), 9.08 (d, J=2.3 Hz, 1H), 9.04 (d, J=1.1 Hz, 1H), 9.02 (d, J=2.3 Hz, 1H), 8.93 (d, J=1.1 Hz, 1H), 7.75 (d, J=8.0 Hz, 2H), 7.49 (d, J=8.0 Hz, 2H), 3.16-3.07 (m, 2H), 2.54-2.42 (m, 1H), 2.11-1.93 (m, 2H), 1.79-1.64 (m, 3H), 1.63-1.20 (m, 3H), 0.89 (t, J=7.1 Hz, 3H). LCMS (Method A): RT=6.23 min; M+H+=382

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resultant residue was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a yellow solid
  8. customThe resultant solid was purified by flash chromatography (silica, Biotage 50 g column, 0-100% (10% methanol in DCM))

Sources & evidence

ORD record
ord-bd83dd3f70004faaa4064fc9ab1263c7
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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