Tetrabutylammonium Fluoride → HCID 58086726, compound

HRID 1098517Notes

Reaction equation

HRID 1098517 reaction equation
[CH3:1][O:2][C:3](=[O:40])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([CH2:13][C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)[CH:21]=3)[N:16]([Si](C(C)C)(C(C)C)C(C)C)[CH:15]=2)[C:7]=1[F:39].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3](=[O:40])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([CH2:13][C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)[CH:21]=3)[NH:16][CH:15]=2)[C:7]=1[F:39]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58086665HCID 58086665, compound

Product 1

HCID 58086726HCID 58086726, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To [2,4-Difluoro-3-(5-pyridin-3-yl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-phenoxy]-acetic acid methyl ester (550, 40.0 mg, 0.071 mmol, prepared as described in Example 65, Scheme 46) in tetrahydrofuran (5.0 mL) was added tetra-n-butylammonium fluoride (22.2 mg, 0.085 mmol). The reaction was stirred at room temperature for 10 minutes. The crude compound was concentrated with silica gel and purified by silica gel column chromatography eluting with 3% methanol in methylene chloride to give the compound as white solid (P-1465, 20 mg, 69%). MS (ESI) [M+H+]+=410.2.

Workup

  1. concentrationThe crude compound was concentrated with silica gel
  2. custompurified by silica gel column chromatography
  3. washeluting with 3% methanol in methylene chloride

Sources & evidence

ORD record
ord-761d787e0c93439f8ad8787ff49a1031
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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