HCID 12751998, compound → HCID 90388426, compound

HRID 2205240Notes

Reaction equation

HRID 2205240 reaction equation
[Li][CH2:2]CCC.[S:6]([N:16]1[CH2:21][C:20](=O)[C:19]2[S:23][CH:24]=[CH:25][C:18]=2[CH2:17]1)([C:9]1[CH:15]=[CH:14][C:12]([CH3:13])=[CH:11][CH:10]=1)(=[O:8])=[O:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:2]=[C:20]1[CH2:21][N:16]([S:6]([C:9]2[CH:15]=[CH:14][C:12]([CH3:13])=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:17][C:18]2[CH:25]=[CH:24][S:23][C:19]1=2

Participants

5

Reactant 2

HCID 12751998HCID 12751998, compoundHCID 178418339Butyllithium

Product 1

HCID 90388426HCID 90388426, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyltriphenylphosphonium bromide (2.05 g, 5.73 mmol, 2.0 equiv) in THF (10.0 mL) at −78° C. was added n-BuLi (3.58 mL, 1.6 M solution, 2.0 equiv) and stirred for 30 min followed by addition of 5,6-dihydro-5-tosylthieno[3,2-c]pyridin-7(4H)-one (880 mg, 2.86 mmol, 1.0 equiv) in THF (5.00 mL). The reaction mixture was stirred at rt for 1 h, then quenched by the addition of a saturated aqueous solution of ammonium chloride. Purification by column chromatography using 5% ethyl acetate in hexanes elution gave 175 mg of the yellow solid, 20%.

Workup

  1. stirringThe reaction mixture was stirred at rt for 1 h
  2. customquenched by the addition of a saturated aqueous solution of ammonium chloride
  3. customPurification by column chromatography
  4. wash5% ethyl acetate in hexanes elution

Sources & evidence

ORD record
ord-c7ffd3f238884dbbbdec7b680956a837
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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