Dimethyl Sulfide → HCID 68546834, compound

HRID 1446664Notes

Reaction equation

HRID 1446664 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][N:9]3[C:12]([C:15]4[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=4)=[CH:13][N:14]=[C:8]3[CH:7]=2)=[CH:2]1.S(C)C.[OH-].[Na+]>C1COCC1>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][N:9]3[C:12]([C:15]4[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=4)=[CH:13][N:14]=[C:8]3[CH:7]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 14798Sodium HydroxideHCID 68546142HCID 68546142, compound

Product 1

HCID 68546834HCID 68546834, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Dissolve 4-(7-thien-3-yl-imidazo[1,2-a]pyridin-3-yl)-benzonitrile (0.087 g, 0.29 mmol) in THF (8 mL). To the solution add a BH3.Me2S solution (2 M, 1.0 mL, 2.0 mmol) at room temperature. Stir the solution for 15 minutes and then heat at 50° C. for 3.5 hours. Cool the mixture at 0° C. and acidify to pH=1 slowly and stir for 30 minutes. Make the reaction mixture basic with solid NaOH to pH=12-14, followed by extraction with ethyl acetate. Wash the extracts with saturated aqueous saturated sodium chloride, dry over MgSO4, filter and evaporate to afford 0.070 g. MS(ES), m/z 306 (M+1).

Workup

  1. additionTo the solution add a BH3
  2. customat room temperature
  3. temperatureCool the mixture at 0° C.
  4. stirringstir for 30 minutes
  5. extractionfollowed by extraction with ethyl acetate
  6. washWash the extracts with saturated aqueous saturated sodium chloride
  7. dry with materialdry over MgSO4
  8. filtrationfilter
  9. customevaporate
  10. customto afford 0.070 g

Sources & evidence

ORD record
ord-9fc51950ab2f4a1080bfa5e0ed9ac6cd
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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