HCID 22638712, compound → HCID 22638753, compound

HRID 2416243Notes

Reaction equation

HRID 2416243 reaction equation
[CH2:1]([Li])CCC.[CH:6]([CH:8]1[CH2:10][CH:9]1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=2)[N:13]([S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH:12]=1)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:28]1([CH3:31])[CH:27]=[CH:26][C:25]([S:22]([N:13]2[C:14]3[C:19](=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=3)[C:11]([CH:9]3[CH2:10][CH:8]3[CH:6]=[CH2:1])=[CH:12]2)(=[O:23])=[O:24])=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 22638712HCID 22638712, compoundHCID 178418339Butyllithium

Product 1

HCID 22638753HCID 22638753, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Butyl lithium (1.4 ml of 2.4M in hexane, 3.36 mmol) was added drop wise over a five min period under a nitrogen atmosphere to a stirred solution of methyltriphenylphosphonium bromide (1.186 g, 3.32 mmol) in dry THF (25 ml). The solution was stirred for 30 min at ambient temperature and then added dropwise to a solution of 3-(2-formyl-cyclopropyl)-1-(toluene-4-sulfonyl)-1H-indole-5-carbonitrile (1.10 g, 3.018 mmol) in 25 ml THF. The mixture was stirred for 24 hr, and then quenched with saturated aqueous ammonium acetate (2 ml). The mixture was concentrated in vacuo and then extracted with ethyl acetate (20 ml). The ethyl acetate extract was washed with water (10 ml), then washed with brine (10 ml), dried over sodium sulfate, and concentrated in vacuo. The residue was chromatographed on silica gel using methylene chloride as the eluent to give 1-(toluene-4-sulfonyl)-3-(2-vinyl-cyclopropyl)-1H-indole-5-carbonitrile (755 mg, 71%). 1H NMR (300 MHz, CDCl3): δ 8.04 (d, 1H), 7.91 (s, 1H), 7.74 (d, 2H), 7.56 (d, 1H), 7.54 (s, 1H), 7.25(m, 2H), 5.57 (m, 1H), 5.19 (d, 1H), 5.01 (d, 1H), 2.36 (s, 3H), 1.86 (m, 1H), 1.63 (m, 1H), 1.16 (m, 2H). MS m/e 363.16 (MH+).

Workup

  1. stirringThe mixture was stirred for 24 hr
  2. customquenched with saturated aqueous ammonium acetate (2 ml)
  3. concentrationThe mixture was concentrated in vacuo
  4. extractionextracted with ethyl acetate (20 ml)
  5. extractionThe ethyl acetate extract
  6. washwas washed with water (10 ml)
  7. washwashed with brine (10 ml)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-c62fab828b274d2aa19cd2e74e46f02d
Source dataset
uspto-grants-2004_11
Patent number
US06822100B2

Reaction notes

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