Triphenylphosphine → HCID 67159279、化合物

HRID 1255191

反応式

HRID 1255191 の反応式
[OH:1][C:2]1[C:7]([I:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([N:15]2[C:19]([C:20]([F:23])([F:22])[F:21])=[C:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:17]=[N:16]2)[CH:12]=[CH:11][CH:10]=1.[CH3:29][C:30]1[CH:37]=[C:36]([CH3:38])[CH:35]=[CH:34][C:31]=1[CH2:32]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl>[CH3:29][C:30]1[CH:37]=[C:36]([CH3:38])[CH:35]=[CH:34][C:31]=1[CH2:32][O:1][C:2]1[C:7]([I:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([N:15]2[C:19]([C:20]([F:23])([F:22])[F:21])=[C:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:17]=[N:16]2)[CH:12]=[CH:11][CH:10]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 278092,4-Dimethylbenzyl alcoholHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 136356801Ethyl 1-[6-(2-hydroxy-3-iodophenyl)pyridin-2-yl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

生成物 1

HCID 67159279HCID 67159279、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of the title compound from Example 15 Step A (200 mg, 0.397 mmol), 2,4-dimethylbenzyl alcohol (81.0 mg, 0.596 mmol), and triphenylphosphine (156 mg, 0.596 mmol) in DCM (2 mL) was added diisopropyl azodicarboxylate (0.114 mL, 0.596 mmol), and the resulting mixture was stirred at ambient temperature. After 18 h, the reaction mixture was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 20% EtOAc in hexanes, then 20 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 594.8 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.17 (s, 1H), 8.02 (d, J=8.0 Hz, 1H), 7.92 (d, J=7.5 Hz, 1H), 7.85-7.81 (m, 2H), 7.60 (d, J=7.5 Hz, 1H), 7.13 (d, J=7.5 Hz, 1H), 7.05 (t, J=7.5 Hz, 1H), 6.95-6.92 (m, 2H), 4.69 (s, 2H), 4.41 (q, J=7.0 Hz, 2H), 2.30 (s, 3H), 2.17 (s, 3H), 1.43 (t, J=7.0 Hz, 3H).

後処理

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customPurification by flash chromatography on silica gel (0 to 20% EtOAc in hexanes

出典と根拠

ORDレコード
ord-54b228aa5b28431eb7c0d5793fb2a938
出典データセット
uspto-grants-2013_06
特許番号
US08455638B2

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