Sodium Carbonate → HCID 69059825, compound

HRID 734832Notes

Reaction equation

HRID 734832 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[CH:22][C:23]([C:26]#[C:27][C:28]3[CH:39]=[CH:38][C:31]4[S:32][C:33]([C:35](O)=[O:36])=[CH:34][C:30]=4[CH:29]=3)=[N:24][CH:25]=2)=[CH:16][CH:15]=1.[BH4-].[Na+].OS([O-])(=O)=O.[K+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:21]=[CH:22][C:23]([C:26]#[C:27][C:28]3[CH:39]=[CH:38][C:31]4[S:32][C:33]([CH2:35][OH:36])=[CH:34][C:30]=4[CH:29]=3)=[N:24][CH:25]=2)=[CH:18][CH:19]=1

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 516920Potassium bisulfateHCID 4311764Sodium borohydrideHCID 69059583HCID 69059583, compound

Product 1

HCID 69059825HCID 69059825, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2.37 g (14.62 mmol) CDI was added to a suspension of 1.9 g (4.87 mmol) of 5-[5-(4-chlorophenyl)pyridin-2-ylethynyl]benzo[b]thiophene-2-carboxylic acid in 40 mL of DMF and the reaction mixture was heated to 50° C. overnight. After cooling to RT, the reaction solution was added to a solution of 552 mg (14.62 mmol) NaBH4 in 5 mL of water in such a way that the temperature did not exceed 30° C. The mixture was stirred for 2 hours at RT, carefully mixed with KHSO4 solution until an acidic reaction was obtained, made basic with saturated sodium carbonate solution, extracted exhaustively with DCM, the combined organic phases were washed twice with water and dried over magnesium sulfate. After the desiccant and solvent had been eliminated, the residue was triturated with PE, suction filtered, and dried in the air. Yield: 1.1 g (60% of theoretical); C22H14ClNOS (M=375.871); calc.: molpeak (M+H)+: 376/378 (Cl); found: molpeak (M+H)+: 376/378 (Cl); HPLC-MS: 6.2 minutes (method B).

Workup

  1. temperatureAfter cooling to RT
  2. customdid not exceed 30° C
  3. customwas obtained
  4. extractionextracted exhaustively with DCM
  5. washthe combined organic phases were washed twice with water
  6. dry with materialdried over magnesium sulfate
  7. customthe residue was triturated with PE, suction
  8. filtrationfiltered
  9. customdried in the air
  10. custom6.2 minutes (method B)

Sources & evidence

ORD record
ord-eb959df3bf724e028bb86b22b474b17d
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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