Dimethylformamide → HCID 58669398, compound

HRID 641632Notes

Reaction equation

HRID 641632 reaction equation
Br[C:2]1[S:14][C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[CH:6]([CH2:15][CH3:16])[N:5]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:4]=2[CH:3]=1.C([Li])CCC.CN(C)[CH:35]=[O:36]>O1CCCC1.C(Cl)Cl>[CH2:15]([CH:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=2[C:13]2[S:14][C:2]([CH:35]=[O:36])=[CH:3][C:4]=2[N:5]1[S:17]([C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)(=[O:19])=[O:18])[CH3:16]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 58669396HCID 58669396, compoundHCID 178418339Butyllithium

Product 1

HCID 58669398HCID 58669398, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-bromo-4-[(4-methoxyphenyl)sulfonyl]-5-ethyl-4,5-dihydrothieno[3,2-c]isoquinoline (2.3 g, 5.0 mmol) in dry tetrahydrofuran (45 mL) was cooled to −78° C. and treated with a solution of butyllithium in hexanes (1.35 M, 3.7 mL, 5.0 mmol) during ca. 2 min followed immediately by the fast addition of dry dimethylformamide (1.9 mL, 25 mmol). After 30 min further at −78° C., the reaction was quenched with 10% aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine (75 mL), dried (MgSO4), and concentrated in vacuo to give the crude product as a light orange solid (2.0 g) which was taken up in methylene chloride (ca. 8 ML) and pre-adsorbed on silica gel (8 g). Flash chromatography on silica gel (72 g) eluting 50-, then 75% methylene chloride-hexane, and then methylene chloride gave the title compound (1.7 g, 81%, m.p. 129-32° C.) as a pale yellow solid.

Workup

  1. customthe reaction was quenched with 10% aqueous ammonium chloride (100 mL)
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined extracts were washed with brine (75 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give the crude product as a light orange solid (2.0 g) which
  7. washFlash chromatography on silica gel (72 g) eluting 50-

Sources & evidence

ORD record
ord-174cf4b753ea4c77b85892b357b35fcb
Source dataset
uspto-grants-2010_04
Patent number
US07696221B2

Reaction notes

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