HCID 11785440, compound → HCID 11339937, compound

HRID 2218515Notes

Reaction equation

HRID 2218515 reaction equation
[C:1]([Cu])#[N:2].[CH3:4][O:5][C:6]([C@H:8]1[N:12]2[C:13](=[O:35])[C:14](Br)=[C:15]([CH2:23][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=[CH:26][CH:25]=3)[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:11]2[S:10][CH2:9]1)=[O:7]>CN1C(=O)CCC1>[CH3:4][O:5][C:6]([C@H:8]1[N:12]2[C:13](=[O:35])[C:14]([C:1]#[N:2])=[C:15]([CH2:23][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=[CH:26][CH:25]=3)[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:11]2[S:10][CH2:9]1)=[O:7]

Participants

4

Reactant 2

HCID 11785440HCID 11785440, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 11339937HCID 11339937, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
220 °C

Procedure

CuCN (120 mg, 1.3 mmol) was added to a stirred solution of 5a (150 mg, 0.30 mmol) in NMP (1.0 mL) at rt. The reaction mixture was heated at 220° C. for 20 min using microwave irradiation and the solvent was then removed by lyophilisation from deionised water. The residue was thoroughly extracted with CH2Cl2, dried and concentrated. Purification by silica gel chromatography (heptane:EtOAc, 1:1) gave 6a as a white foam (110 mg, 82%)[α]D −83 (c 1.0, CHCl3); IR λ 3012, 2956, 2217, 1751, 1654, 1486, 1442, 1369 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.79 (d, J=7.8, 1H), 7.70 (d, J=8.1, 1H), 7.62 (d, J=8.2, 1H), 7.47-7.29 (m, 3H), 7.19-6.92 (m, 5H), 6.87 (d, J=7.3, 1H), 5.79 (dd, J=8.9, 2.3, 1H), 4.41-4.27 (m, 2H), 3.89 (s, 3H), 3.75 (dd, J=11.9, 8.9, 1H), 3.52 (dd, J=11.9, 2.3, 1H); 13C NMR (100 MHz, CDCl3) δ 167.6, 160.7, 158.7, 155.2, 134.4, 133.6, 132.4, 131.4, 129.7, 129.2, 128.8 (broad and splitted), 128.6, 127.6, 126.1, 125.7, 125.3, 125.2, 122.7, 117.1, 115.2, 101.3, 64.4, 53.7, 35.3, 31.8; HRMS (EI+) calcd for C27H20N2O3S 452.1195, obsd 452.1192.

Workup

  1. custommicrowave irradiation
  2. customthe solvent was then removed by lyophilisation from deionised water
  3. extractionThe residue was thoroughly extracted with CH2Cl2
  4. customdried
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (heptane:EtOAc, 1:1)

Sources & evidence

ORD record
ord-aafa4940110640e083f474b4bf0133b3
Source dataset
uspto-grants-2008_08
Patent number
US07411066B2

Reaction notes

Loading…