Tetrahydrofuran → 2-[(E)-2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine

HRID 1515888Notes

Reaction equation

HRID 1515888 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:20]([C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)=[CH:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[Cl-].[Na+].O>[CH:22]1(/[CH:21]=[C:20](/[C:11]2[NH:10][C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=2)\[C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 672293051-benzenesulfonyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 532502852-[(E)-2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridineYield 100.6%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 1-benzenesulfonyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine (200 mg, 0.38 mmol) and tetrabutylammonium fluoride in tetrahydrofuran (1 M, 7.6 mL, 7.6 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 (3×20 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo to give 2-[(E)-2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine (147 mg, 100%) as a solid which was used in the next step without purification: LC/MS m/e calcd for C21H21FN2O2S [M+H]+ 385.48, observed 385.2; 1H NMR (400 MHz, MeOD) δ ppm 8.04 (d, J=8.3 Hz, 3H), 7.51-7.56 (m, 3H), 6.45 (d, J=10.1 Hz, 1H), 5.77 (s, 1H), 3.32 (br. s., 1H), 3.16-3.20 (m, 3H), 2.37-2.44 (m, 1H), 1.72-1.82 (m, 4H), 1.45-1.57 (m, 4H).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washwashed with a saturated aqueous ammonium chloride solution (3×20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d872576a45474bf6b5b4879d78bc104c
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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