Dimethylformamide → HCID 71262265, compound

HRID 540265Notes

Reaction equation

HRID 540265 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:14]2[CH2:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[S:17](=[O:26])(=[O:25])[CH2:16][CH2:15]2)[CH:3]=1.[C:27]([O:31][CH2:32][CH3:33])(=[O:30])[CH:28]=[CH2:29].C(N(CC)CC)C.CN(C)C=O>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.O>[O:25]=[S:17]1(=[O:26])[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[CH2:20][N:14]([C:4]2[CH:3]=[C:2](/[CH:29]=[CH:28]/[C:27]([O:31][CH2:32][CH3:33])=[O:30])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH3:13])[CH:10]=3)[N:5]=2)[CH2:15][CH2:16]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 71255557HCID 71255557, compound

Product 1

HCID 71262265HCID 71262265, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(4-chloro-6-ethylquinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide (300 mg, 0.78 mmol), ethyl prop-2-enoate (170 mg, 1.70 mmol), triethylamine (1 mL) and N,N-dimethylformamide (2 mL), bis(tri-tert-butylphosphine)palladium(0) (15 mg, 0.02 mmol) was heated with stirring in a 10 mL of microwave process vial for 30 minutes at 100° C. under microwave irradiation. The reaction mixture was poured into water (5 mL) and extracted with ethyl acetate (10 mL×3). The organic layers were combined, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluting with 20-40% ethyl acetate in petroleum ether) to afford 280 mg of the product as a white solid (yield was 80%). MS obsd. (ESI+) [(M+H)+] 451.

Workup

  1. temperaturewas heated
  2. extractionextracted with ethyl acetate (10 mL×3)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (eluting with 20-40% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-5267216ef20e4fa7b4939d922502b8c5
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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