Hydrochloric Acid → HCID 86707266, compound

HRID 576047Notes

Reaction equation

HRID 576047 reaction equation
N1C=CC=CC=1.[F:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1.[Br:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][N:22]([C:26](=[O:31])[C:27]([F:30])([F:29])[F:28])[CH2:23]2)=[CH:18][C:17]=1[S:32](Cl)(=[O:34])=[O:33].Cl>C(Cl)(Cl)Cl>[Br:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][N:22]([C:26](=[O:31])[C:27]([F:29])([F:28])[F:30])[CH2:23]2)=[CH:18][C:17]=1[S:32]([NH:12][C:11]1[CH:13]=[CH:14][C:8]([F:7])=[CH:9][CH:10]=1)(=[O:33])=[O:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 97314-FluoroanilineHCID 86707265HCID 86707265, compound

Product 1

HCID 86707266HCID 86707266, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Pyridine (3.09 mL, 38.4 mmol) was added to a solution of 4-fluoroaniline (3.73 g, 33.6 mmol) in chloroform (107 mL), and 7-bromo-2-(trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-6-sulfonyl chloride (13.0 g, 32.0 mmol) was added thereto while cooling in ice. The mixture was warmed to room temperature and stirred for 13 hr. To the mixture was added 1 mol/L hydrochloric acid, and the mixture was extracted with chloroform. The organic layer was concentrated under reduced pressure and the concentrate was powdered with hexane and ethyl acetate (4:1) and then collected by filtration to afford 7-bromo-N-(4-fluorophenyl)-2-(trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-6-sulfonamide as an orange powder (14.5 g).

Workup

  1. additionwas added
  2. temperaturewhile cooling in ice
  3. extractionthe mixture was extracted with chloroform
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-f128fe690b0d4dec9c11bf728350544b
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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