Tetrabutylammonium Fluoride → 4-{2-Cyano-5-[5-(4-hydroxy-piperidin-1-yl)-3H-imidazo[4,5-b]pyridine-2-carbonyl]-phenyl}-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester

HRID 1909065Notes

Reaction equation

HRID 1909065 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2=[CH:13][N:14]=[CH:15][C:16]([C:17]3[CH:22]=[C:21]([C:23]([C:25]4[NH:57][C:28]5=[N:29][C:30]([N:33]6[CH2:38][CH2:37][CH:36]([O:39][Si](C(C)(C)C)(C7C=CC=CC=7)C7C=CC=CC=7)[CH2:35][CH2:34]6)=[CH:31][CH:32]=[C:27]5[N:26]=4)=[O:24])[CH:20]=[CH:19][C:18]=3[C:58]#[N:59])=[C:11]2[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:12]2=[CH:13][N:14]=[CH:15][C:16]([C:17]3[CH:22]=[C:21]([C:23]([C:25]4[NH:57][C:28]5=[N:29][C:30]([N:33]6[CH2:34][CH2:35][CH:36]([OH:39])[CH2:37][CH2:38]6)=[CH:31][CH:32]=[C:27]5[N:26]=4)=[O:24])[CH:20]=[CH:19][C:18]=3[C:58]#[N:59])=[C:11]2[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178451568HCID 178451568, compound

Product 1

HCID 1784515664-{2-Cyano-5-[5-(4-hydroxy-piperidin-1-yl)-3H-imidazo[4,5-b]pyridine-2-carbonyl]-phenyl}-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl esterYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(5-{5-[4-(tert-Butyl-diphenyl-silanyloxy)-piperidin-1-yl]-3H-imidazo[4,5-b]pyridine-2-carbonyl}-2-cyano-phenyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester in THF (0.2M) was added a 1M TBAF in THF solution at 23° C. After 24 hr, the reaction was quenched with sat'd NaHCO3 and extracted with EtOAc (3×), the combined organics washed with brine, dried over Na2SO4, filtered, and concentrated to a red solid. The crude was purified using chromatography eluting with MeOH/DCM mixtures giving 4-{2-Cyano-5-[5-(4-hydroxy-piperidin-1-yl)-3H-imidazo[4,5-b]pyridine-2-carbonyl]-phenyl}-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester as a red-orange solid (420 mg, 0.738 mmol, 66%). MS ESI m/z 564.5 (M+H)+.

Workup

  1. customthe reaction was quenched with sat'd NaHCO3
  2. extractionextracted with EtOAc (3×)
  3. washthe combined organics washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to a red solid
  7. customThe crude was purified
  8. washeluting with MeOH/DCM

Sources & evidence

ORD record
ord-890ca9d2bc7740ce9944e415faa980f5
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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