Water → HCID 59506837, compound

HRID 1261138Notes

Reaction equation

HRID 1261138 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]3[C:28]4[C:23](=[N:24][CH:25]=[CH:26][CH:27]=4)[N:22]([Si](C(C)C)(C(C)C)C(C)C)[CH:21]=3)=[CH:15][CH:14]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[NH:22]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:28]2[C:20]([CH2:19][C:16]2[CH:17]=[CH:18][C:13]([NH:12][C:10]([NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:40])([F:1])[F:39])[CH:4]=3)=[O:11])=[CH:14][CH:15]=2)=[CH:21]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 59506799HCID 59506799, compound

Product 1

HCID 59506837HCID 59506837, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3-Trifluoromethyl-phenyl)-3-[4-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-phenyl]-urea (114, 85.0 mg, 0.150 mmol) was dissolved in tetrahydrofuran (10.0 mL) and tetra-n-butylammonium fluoride (52.2 mg, 0.200 mmol) was added. After 10 minutes, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified with by silica gel chromatography to give the compound (P-0262, 23 mg, 38% over steps 6 & 7). MS (ESI) [M+H+]+=411.2

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified with by silica gel chromatography
  6. customto give the compound (P-0262, 23 mg, 38% over steps 6 & 7)

Sources & evidence

ORD record
ord-f876cfa4f64448da909fe72575964e37
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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