Sodium Carbonate → HCID 86633490, 화합물

HRID 1255165

반응식

HRID 1255165 반응식
Br[C:2]1[CH:35]=[CH:34][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[N:19]=[C:18]([N:20]3[C:24]([C:25]([F:28])([F:27])[F:26])=[C:23]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:22]=[N:21]3)[CH:17]=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.[F:36][C:37]([F:50])([F:49])[C:38]1[CH:43]=[CH:42][C:41]([CH:44]=[CH:45]B(O)O)=[CH:40][CH:39]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[F:26][C:25]([F:28])([F:27])[C:24]1[N:20]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:7][CH2:6][C:5]3[CH:34]=[CH:35][C:2](/[CH:45]=[CH:44]/[C:41]4[CH:40]=[CH:39][C:38]([C:37]([F:36])([F:49])[F:50])=[CH:43][CH:42]=4)=[CH:3][CH:4]=3)[N:19]=2)[N:21]=[CH:22][C:23]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 4573116(4-(Trifluoromethyl)styryl)boronic acidHCID 67159752Ethyl 1-(6-{2-[(4-bromobenzyl)oxy]phenyl}pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

생성물 1

HCID 86633490HCID 86633490, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a vial containing the title compound from Example 2 Step A (50.0 mg, 0.092 mmol) were added 2-(4-trifluoromethylphenyl)vinyl boronic acid (29.6 mg, 0.137 mmol) and trans-dichlorobis(triphenylphosphine) palladium (II) (6.4 mg, 0.009 mmol). Acetonitrile (0.400 mL) and sodium carbonate (0.229 mL, 1.0 M aqueous, 0.229 mmol) were added, and the resulting mixture was degassed via nitrogen sparge. The reaction vial was capped and placed in a pre-heated oil bath (70° C.). After 18 h, the reaction mixture was allowed to cool to ambient temperature and was poured into water. The mixture was extracted with DCM, and the organic phase was concentrated in vacuo. Purification by chromatography on silica gel (0 to 30% EtOAc in hexanes, then 30 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 638.4 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.16 (d, J=8.0 Hz, 1H), 8.13 (s, 1H), 7.97 (d, J=7.5 Hz, 1H), 7.88 (t, J=7.5 Hz, 1H), 7.61 (br s, 4H), 7.54 (d, J=8.0 Hz, 1H), 7.52 (d, J=8.5 Hz, 2H), 7.41-7.39 (m, 1H), 7.37 (d, J=7.5 Hz, 1H), 7.21-7.06 (m, 4H), 5.18 (s, 2H), 4.38 (q, J=7.0 Hz, 2H), 1.39 (t, J=7.0 Hz, 3H).

후처리

  1. customthe resulting mixture was degassed via nitrogen
  2. customsparge
  3. customThe reaction vial was capped
  4. customplaced in a pre-heated oil bath
  5. custom(70° C.)
  6. additionwas poured into water
  7. extractionThe mixture was extracted with DCM
  8. concentrationthe organic phase was concentrated in vacuo
  9. customPurification by chromatography on silica gel (0 to 30% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-0ca67ef807f64216b7fd49d8799cbab2
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455638B2

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