Water → HCID 10225015, compound

HRID 585016Notes

Reaction equation

HRID 585016 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:20]=[C:19]3[C:15]([CH:16]=[C:17]([C:24]4[C:25](=[O:34])[NH:26][C:27]5[C:32]([CH:33]=4)=[CH:31][CH:30]=[CH:29][CH:28]=5)[N:18]3C([O-])=O)=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].O.CSC.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][S:2]([N:5]1[CH2:6][CH2:7][N:8]([CH2:11][C:12]2[CH:20]=[C:19]3[C:15]([CH:16]=[C:17]([C:24]4[C:25](=[O:34])[NH:26][C:27]5[C:32]([CH:33]=4)=[CH:31][CH:30]=[CH:29][CH:28]=5)[NH:18]3)=[CH:14][CH:13]=2)[CH2:9][CH2:10]1)(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 1068Dimethyl SulfideHCID 6422Trifluoroacetic acidHCID 22341792HCID 22341792, compound

Product 1

HCID 10225015HCID 10225015, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boc-indole 2-3 (120 mg, 0.22 mmol) was slurried in 3 mL of CH2Cl2, H2O (10 μL) and dimethylsulfide (10 μL). TFA (3 mL) was added and the reaction was observed to become homogenous. The reaction was then stirred for 1.5 hours. The excess TFA/CH2Cl2 was removed under reduced pressure. The residue was dissolved in DMSO and purified via reverse phase HPLC (95%-5% H2O/AcCN). The pure fractions were combined in a separatory funnel and the pH adjusted to 11 by the addition of 0.5N NaOH. The mixture was then extracted with CH2Cl2/nBuOH (3:1, 2×100 mL). The organic layer was washed with brine, dried with Na2SO4 and concentrated to give 2-4 as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 11.43 (s, 1H), 8.52 (s, 1H), 7.73 (d, 1H, J=7.8 Hz), 7.51 (d, 2H, J=7.3 Hz), 7.44 (bs, 1H), 7.37 (d, 1H, J=8.1 Hz), 7.31 (bs, 1H), 7.24 (t, 1H, J=7.3 Hz), 6.98 (d, 1H, J=7.6 Hz), 3.62 (s, 2H), 3.12 (m, 4H), 2.87 (s, 3H), 2.48 (m, 4H).

Workup

  1. customThe excess TFA/CH2Cl2 was removed under reduced pressure
  2. dissolutionThe residue was dissolved in DMSO
  3. custompurified via reverse phase HPLC (95%-5% H2O/AcCN)
  4. customThe pure fractions were combined in a separatory funnel
  5. additionthe pH adjusted to 11 by the addition of 0.5N NaOH
  6. extractionThe mixture was then extracted with CH2Cl2/nBuOH (3:1, 2×100 mL)
  7. washThe organic layer was washed with brine
  8. dry with materialdried with Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b1ba3efcf7cc4824be41fc86b5e4b4e6
Source dataset
uspto-grants-2005_08
Patent number
US06927293B2

Reaction notes

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