HCID 66966005, compound → HCID 66965642, compound

HRID 1514963Notes

Reaction equation

HRID 1514963 reaction equation
[C:1]([O:5][C:6](=[O:41])[CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][C:21]([C:24](=[O:36])[NH:25][C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=3)=[CH:20][C:19]=2[N+:37]([O-])=O)=[C:11]([Cl:40])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>C(OP(OCC)OCC)C>[C:1]([O:5][C:6](=[O:41])[CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([C:16]2[NH:37][C:19]3[C:18]([CH:17]=2)=[CH:23][CH:22]=[C:21]([C:24](=[O:36])[NH:25][C:26]2[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=2)[CH:20]=3)=[C:11]([Cl:40])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 66966005HCID 66966005, compound

Product 1

HCID 66965642HCID 66965642, compound

Reagents, catalysts & solvents 1

HCID 31215Triethyl phosphiteSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 3-(3,5-dichloro-4-{(E)-2-[2-nitro-4-(quinolin-2-ylcarbamoyl)-phenyl]-vinyl}-phenyl)-propionic acid tert-butyl ester (200 mg, 0.34 mmol) was added triethylphosphite (300 μL) and the mixture was stirred at 160° C. for 3 h. The solvent was removed under reduced pressure and the residue was taken up in toluene and concentrated twice. The crude material was purified by flash chromatography on silica gel, eluting with a gradient of 2-100% ethyl acetate/heptane to obtain 3-{3,5-dichloro-4-[6-(quinolin-2-ylcarbamoyl)-1H-indol-2-yl]-phenyl}-propionic acid tert-butyl ester as a yellow solid. MS (m/z) 560.2 (M+1); 1H NMR (DMSO-d6, 400 MHz) δ 11.81 (d, J=1.52 Hz, 1H), 11.04 (s, 1H), 8.39 (s, 2H), 8.20 (s, 1H), 7.94 (d, J=1.14 Hz, 1H), 7.88 (d, J=8.08 Hz, 1H), 7.80 (dd, J=8.34, 1.52 Hz, 1H), 7.73 (ddd, J=8.37, 6.92, 1.39 Hz, 1H), 7.68 (d, J=8.46 Hz, 1H), 7.55 (s, 2H), 7.52 (t, J=6.95 Hz, 1H), 6.57 (d, J=1.39 Hz, 1H), 2.90 (t, J=7.33 Hz, 2H), 2.62 (t, J=7.45 Hz, 2H), 1.40 (s, 9H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. concentrationconcentrated twice
  3. customThe crude material was purified by flash chromatography on silica gel
  4. washeluting with a gradient of 2-100% ethyl acetate/heptane

Sources & evidence

ORD record
ord-f82d82ee9dac4b738f67622acfff1e15
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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