Hydrogen Bromide → HCID 24775392, compound

HRID 1159787Notes

Reaction equation

HRID 1159787 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[N:15]1([CH2:22][C:23]2[CH:31]=[C:30]([O:32]C)[CH:29]=[C:28]3[C:24]=2[CH:25]=[CH:26][N:27]3[S:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)(=[O:36])=[O:35])[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.Br.C([O-])(O)=O.[Na+]>C(O)(=O)C>[N:15]1([CH2:22][C:23]2[CH:31]=[C:30]([OH:32])[CH:29]=[C:28]3[C:24]=2[CH:25]=[CH:26][N:27]3[S:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)(=[O:36])=[O:35])[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide3×HCID 516892Sodium BicarbonateHCID 86618243HCID 86618243, compound

Product 1

HCID 24775392HCID 24775392, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Conditions

Temperature
125 °C

Procedure

To 4-(1,4-Diazepan-1-ylmethyl)-6-methoxy-1-(phenylsulfonyl)-1H-indole (0.12 g, 0.03 mmol; Example 58) was 33% HBr in acetic acid (2 mL) added and the mixture was refluxed in STEM-block at 125° C. for 20 h which gave 70% conversion to product. Additional HBr in acetic acid (1 mL) was added and the mixture was refluxed for additional 20 h which gave 90% conversion product. Additional HBr in acetic acid (1 mL) was added and the mixture was refluxed for additional 21 h. The mixture was cooled to rt and sat. NaHCO3-solution was added (foaming) until neutral pH. The mixture was extracted with 3*EtOAc/ethanol (10:1). The organic layers were dried (Na2SO4), filtrated and the solvent was evaporated yielding 9.5 mg (82%) of a brownish-red solid. MS (ESI+) for C20H23N3O3S m/z 386 (M+H)+.

Workup

  1. additionadded
  2. customgave 70% conversion to product
  3. temperaturethe mixture was refluxed for additional 20 h which
  4. customgave 90% conversion product
  5. temperaturethe mixture was refluxed for additional 21 h
  6. temperatureThe mixture was cooled to rt
  7. extractionThe mixture was extracted with 3*EtOAc/ethanol (10:1)
  8. dry with materialThe organic layers were dried (Na2SO4)
  9. filtrationfiltrated
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-88285d4243224e509d6f522c809fefc6
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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