Trifluoroacetic acid → HCID 58221390, compound

HRID 1618753Notes

Reaction equation

HRID 1618753 reaction equation
[S:1]1[CH2:6][CH2:5][CH:4]([CH:7]=O)[CH2:3][CH2:2]1.Cl.[Br:10][C:11]1[CH:12]=[C:13]([NH:17]N)[CH:14]=[CH:15][CH:16]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:10][C:11]1[CH:12]=[C:13]2[N:17]=[CH:7][C:4]3([CH2:5][CH2:6][S:1][CH2:2][CH2:3]3)[C:14]2=[CH:15][CH:16]=1.[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]2[N:17]=[CH:7][C:4]3([CH2:5][CH2:6][S:1][CH2:2][CH2:3]3)[C:12]=12

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 337573-Bromophenylhydrazine hydrochlorideHCID 20143720Thiane-4-carbaldehyde

Product 2

HCID 58221390HCID 58221390, compoundHCID 58221564HCID 58221564, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred ice cooled solution of tetrahydro-2H-thiopyran-4-carbaldehyde (2.1 g, 16.1 mmol) in DCM (30 mL) was added 3-bromophenylhydrazine hydrochloride (1.0 eq., 3.6 g) in one portion. The resulting mixture was stirred at 0° C. for 10 min before TFA (3.0 eq., 5.52 g) was added dropwise via syringe. The resulting mixture was stirred at 0° C. for 10 min and then at rt for 4 h. After this time the mixture was poured into ice and NH3H2O (28%) and extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was dissolved in benzene and evaporated in vacuo to give 6-bromo-2′,3′,5′,6′-tetrahydrospiro[indole-3,4′-thiopyran] and 4-bromo-2′,3′,5′,6′-tetrahydrospiro[indole-3,4′-thiopyran] in a ratio of 1 to 1.3. Mass Spectrum (ESI) m/e=282.0 [(M+1) (79Br)] and 284.0 [(M+1) (81Br)].

Workup

  1. additionwas added dropwise via syringe
  2. waitat rt for 4 h
  3. additionAfter this time the mixture was poured into ice and NH3H2O (28%)
  4. extractionextracted with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in benzene
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-e0bb5803b30744b7a3df90986f1a466c
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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