Sodium Iodide → HCID 11624273, compound

HRID 746621Notes

Reaction equation

HRID 746621 reaction equation
[Na+].[I-].C[Si](Cl)(C)C.[N:8]1([CH2:13][CH2:14][C:15]2[S:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[C:16]=2[C:24]([C:27]2[N:28]=[CH:29][S:30][CH:31]=2)(O)[CH3:25])[CH2:12][CH2:11][CH2:10][CH2:9]1.S([O-])([O-])(=O)=S.[Na+].[Na+].[NH4+].[OH-]>C(#N)C.ClCCl>[N:8]1([CH2:13][CH2:14][C:15]2[S:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[C:16]=2[C:24]([C:27]2[N:28]=[CH:29][S:30][CH:31]=2)=[CH2:25])[CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 14923Ammonium HydroxideHCID 24477Sodium ThiosulfateHCID 11566634HCID 11566634, compound

Product 1

HCID 11624273HCID 11624273, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

NaI was taken up in acetonitrile (30 mL) under N2 and trimethylsilyl chloride was slowly added (2.97 mL, 24 mmol). The mixture was stirred for 15 min after which a solution of 1-[2-(2-pyrrolidin-1-yl-ethyl)-benzo[b]thiophen-3-yl]-1-thiazol-4-yl-ethanol (1.4 g, 3.91 mmol) in acetonitrile (30 mL) and dichloromethane (10 mL) was added. The reaction was heated in a closed vessel to 100° C. for 3 hrs. After cooling to room temperature 1M sodium thiosulfate was added followed by NH4OH until pH ˜9. After extraction with EtOAc, drying (MgSO4), filtering, concentration in vacuo and subsequently purification by mass triggered preparative HPLC, 4-{1-[2-(2-pyrrolidin-1-yl-ethyl)-benzo[b]thiophen-3-yl]-vinyl}-thiazole (Compound 19-3) was isolated MH+=341.

Workup

  1. additionwas added
  2. additionwas added
  3. extractionAfter extraction with EtOAc
  4. dry with materialdrying (MgSO4)
  5. filtrationfiltering
  6. concentrationconcentration
  7. customin vacuo and subsequently purification by mass

Sources & evidence

ORD record
ord-888ad8cf5f4d471a860a483a5bc3d605
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

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