Tetrahydrofuran → 4-[2-cyclopentyl-1-(5-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-2-fluoro-benzoic acid methyl ester

HRID 1515927Notes

Reaction equation

HRID 1515927 reaction equation
[CH3:1][O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:17]2[N:26](S(C3C=CC=CC=3)(=O)=O)[C:20]3=[N:21][CH:22]=[C:23]([CH3:25])[CH:24]=[C:19]3[CH:18]=2)=[CH:11][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:6][C:5]=1[F:36].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[Cl-].[Na+].O>[CH3:1][O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:17]2[NH:26][C:20]3=[N:21][CH:22]=[C:23]([CH3:25])[CH:24]=[C:19]3[CH:18]=2)=[CH:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)=[CH:6][C:5]=1[F:36]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 672291634-[1-(1-benzenesulfonyl-5-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-2-fluoro-benzoic acid methyl ester

Product 1

HCID 672277824-[2-cyclopentyl-1-(5-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-2-fluoro-benzoic acid methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 4-[1-(1-benzenesulfonyl-5-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-2-fluoro-benzoic acid methyl ester (470 mg, 1.99 mmol) and a solution of tetrabutylammonium fluoride in tetrahydrofuran (1 M, 39.8 mL, 39.8 mmol) was stirred for 12 h at room temperature. The mixture was poured into brine (15 mL), extracted with ethyl acetate (2×50 mL), washed with a saturated aqueous ammonium chloride solution (3×30 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo to give 4-[2-cyclopentyl-1-(5-methyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-2-fluoro-benzoic acid methyl ester (0.75 g, 100%) as a solid which was used in the next step without purification: LC/MS m/e calcd for C23H23FN2O2 [M+H]+ 379.45, observed 378.9.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washwashed with a saturated aqueous ammonium chloride solution (3×30 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-341e5c41662b4294b81a591990b83ca3
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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