8-bromo-N-(2,4-difluorophenyl)-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide → HCID 57900388, compound

HRID 628117Notes

Reaction equation

HRID 628117 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[O:8][CH2:7][C:6]3[CH:12]=[C:13]([C:15]([N:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=4[F:26])[CH3:18])=[O:16])[S:14][C:5]=3[C:4]=2[CH:3]=1.[Cu](C#N)[C:28]#[N:29]>CN(C)C=O.[Cl-].[NH4+].[OH-].[NH4+]>[C:28]([C:2]1[CH:11]=[CH:10][C:9]2[O:8][CH2:7][C:6]3[CH:12]=[C:13]([C:15]([N:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=4[F:26])[CH3:18])=[O:16])[S:14][C:5]=3[C:4]=2[CH:3]=1)#[N:29]

Participants

6

Reactant 2

HCID 579003378-bromo-N-(2,4-difluorophenyl)-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamideHCID 178418260HCID 178418260, compound

Product 1

HCID 57900388HCID 57900388, compoundYield 79.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 14923Ammonium HydroxideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A solution of 8-bromo-N-(2,4-difluorophenyl)-N-methyl-4H-thieno[3,2-c]chromene-2-carboxamide 160bp (33.7 mg, 0.0772 mmol, 1 equiv) and copper cyanide (22 mg, 0.24 mmol, 3.2 equiv) in N,N-dimethylformamide (1 mL) was heated at 250° C. in the microwave for 30 min. The reaction mixture was diluted with 9:1 saturated aqueous ammonium chloride solution/ammonium hydroxide (10 mL). The resulting mixture was extracted with dichloromethane (3×5 mL). The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (11:4/hexanes:ethylacetate) provided 161bp as a white solid (23.4 mg, 79%). 1H NMR (500 MHz, CDCl3) δ 7.40-7.42 (m, 2H), 7.32 (m, 1H), 6.99 (t, J=8.1 Hz, 1H), 6.92 (m, 1H), 6.88 (s, 1H), 5.23 (s, 2H), 3.40 (s, 3H). LCMS (ESI) m/z: 383.1

Workup

  1. extractionThe resulting mixture was extracted with dichloromethane (3×5 mL)
  2. dry with materialThe collected organic was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (11:4/hexanes:ethylacetate)

Sources & evidence

ORD record
ord-73edf33eebab4f158b1ac04f34ac22a1
Source dataset
uspto-grants-2016_04
Patent number
US09309265B2

Reaction notes

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