Tetrabutylammonium Fluoride → 2-fluoro-4-[1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-vinyl]-benzoic acid methyl ester

HRID 1515828Notes

Reaction equation

HRID 1515828 reaction equation
[CH3:1][O:2][C:3](=[O:38])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:18]2[N:27](S(C3C=CC=CC=3)(=O)=O)[C:21]3=[N:22][CH:23]=[C:24]([F:26])[CH:25]=[C:20]3[CH:19]=2)=[CH:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:6][C:5]=1[F:37].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3](=[O:38])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:18]2[NH:27][C:21]3=[N:22][CH:23]=[C:24]([F:26])[CH:25]=[C:20]3[CH:19]=2)=[CH:11][CH:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[CH:6][C:5]=1[F:37]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 672296664[1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-vinyl]-2-fluoro-benzoic acid methyl ester

Product 1

HCID 672294732-fluoro-4-[1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-vinyl]-benzoic acid methyl esterYield 84.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4[1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-vinyl]-2-fluoro-benzoic acid methyl ester (400 mg, 0.74 mmol) and tetrabutylammonium fluoride solution in tetrahydrofuran (1 M, 4 ml) was stirred at 25° C. for 16 h. The reaction was quenched with a saturated aqueous ammonium chloride solution (20 mL). The mixture was extracted with ethyl acetate (2×100 mL), washed with a saturated aqueous ammonium chloride solution (3×50 mL), brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 2-fluoro-4-[1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-vinyl]-benzoic acid methyl ester (250 mg, 84%) as a solid which was used in the next step without further purification: LC/MS m/e calcd for C22H20F2N2O3 [M+H] 399.41, observed 399.0.

Workup

  1. customThe reaction was quenched with a saturated aqueous ammonium chloride solution (20 mL)
  2. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
  3. washwashed with a saturated aqueous ammonium chloride solution (3×50 mL), brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3c340515a4fa40439c5725321199c51e
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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