Water → HCID 59506837, compound

HRID 250682Notes

Reaction equation

HRID 250682 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-d5333527126f4d16b4ea0da6483db42f
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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