HCID 86607511, compound → HCID 67234086, compound

HRID 1465942Notes

Reaction equation

HRID 1465942 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10](Br)[C:9]2[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:26])=[O:5])[CH3:2].[Cu][C:28]#[N:29]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([C:28]#[N:29])[C:9]2[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:26])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 86607511HCID 86607511, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 67234086HCID 67234086, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 4-bromo-7-hydroxy-2-(3-trifluoromethyl-phenyl)-thieno[3,2-c]pyridine-6-carboxylic acid ethyl ester (example 25.a, 108 mg, 0.24 mmol) and copper(I) cyanide (45 mg, 0.5 mmol) suspended in 1 mL DMF was heated at 135° C. for 15 minutes in a CEM microwave reactor. The resultant mixture was partitioned between ethyl acetate and water, and the organic fraction was washed with brine, dried over anhydrous sodium sulfate, and concentrated to a crude residue. The desired product was purified by column chromatography eluting from silica gel with a gradient of 10-60% ethyl acetate in hexanes to give 48 mg of a white solid; MS: (+) m/z 392.9 (M+1)

Workup

  1. customThe resultant mixture was partitioned between ethyl acetate and water
  2. washthe organic fraction was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated to a crude residue
  5. customThe desired product was purified by column chromatography
  6. washeluting from silica gel with a gradient of 10-60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-3f479dc8e39e4b078b1a778e5fc4c40c
Source dataset
uspto-grants-2015_04
Patent number
US09000006B2

Reaction notes

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