HCID 86601724, compound → HCID 57592472, compound

HRID 1784418Notes

Reaction equation

HRID 1784418 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[S:14](F)(=[O:16])=[O:15])[CH2:10][N:9](C(=O)C(F)(F)F)[CH2:8][CH2:7]2)[CH3:2].[F:24][C:25]1[CH:30]=[CH:29][C:28]([Mg]Br)=[CH:27][CH:26]=1>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[S:14]([C:28]1[CH:29]=[CH:30][C:25]([F:24])=[CH:26][CH:27]=1)(=[O:15])=[O:16])[CH2:10][NH:9][CH2:8][CH2:7]2)[CH3:2]

Participants

4

Reactant 2

HCID 86601724HCID 86601724, compoundHCID 178418676HCID 178418676, compound

Product 1

HCID 57592472HCID 57592472, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice bath cooled solution of 6-ethoxy-2-(2,2,2-trifluoro-ethanoyl)-1,2,3,4-tetrahydro-isoquinoline-7-sulfonyl fluoride (1.30 g, 3.66 mmol) in THF (13 mL) was added dropwise 4-fluorophenylmagnesium bromide (18.3 mL, 18.3 mmol). The mixture was stirred at room temperature overnight before quenching with aqueous sodium potassium tartrate tetrahydrate (13 g). The aqueous was extracted twice with diethyl ether. The organics were combined, dried and evaporated to dryness. The resulting oil was purified by chromatography on silica, eluting with 1 to 10% MeOH/NH3 in dichloromethane to yield the title compound D31 as a solid (700 mg). MH+ 336. 1H NMR δ (CDCl3)1.22-1.37 (3H, t), 2.74-2.91 (2H, m), 3.08-3.19 (2H, t), 4.01 (2H, s), 4.13-4.25 (2H, m), 6.58 (1H, s), 7.06-7.20 (2H, m), 7.83 (1H, s), 7.91-8.01 (2H, m).

Workup

  1. custombefore quenching with aqueous sodium potassium tartrate tetrahydrate (13 g)
  2. extractionThe aqueous was extracted twice with diethyl ether
  3. customdried
  4. customevaporated to dryness
  5. customThe resulting oil was purified by chromatography on silica
  6. washeluting with 1 to 10% MeOH/NH3 in dichloromethane

Sources & evidence

ORD record
ord-df9872deb0d9445d87ae5d0d8f80d9ae
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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