Sodium Carbonate → HCID 68702253、化合物

HRID 42639ノート

反応式

HRID 42639 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:21]1[CH:22]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[N:28]=2)[CH:24]=[CH:25][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:25]2[CH:26]=[CH:21][CH:22]=[C:23]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:34])[F:35])[N:28]=3)[CH:24]=2)=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 106826034-(Benzyloxy)-3-methoxybenzeneboronic acidHCID 686995402-(3-Bromophenyl)-6-(trifluoromethyl)pyridine

生成物 1

HCID 68702253HCID 68702253、化合物

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

To a stirred solution of 4-benzyloxy-3-methoxyphenylboronic acid (1.0 g, 3.87 mmol) and 2-(3-bromophenyl)-6-(trifluoromethyl)pyridine (1.063 g, 3.52 mmol) in toluene (10 mL) and ethanol (1 mL) at room temperature under argon was added 2 N aqueous sodium carbonate solution (5.41 mL, 10.82 mmol) followed by tetrakis(triphenylphosphine)palladium (0.22 g, 0.19 mmol). The resulting mixture was stirred at 90° C. for two hours and then allowed to cool to room temperature. The phases were separated and the aqueous phase was extracted with toluene (5 mL). The combined organic phases were washed with water and brine, then dried over anhydrous sodium sulphate and filtered. Evaporation of the solvent left a brown oil that was chromatographed over silica gel (petroleum ether/ethyl acetate, 9:1) to give 2-(4′-(benzyloxy)-3′-methoxybiphenyl-3-yl)-6-(trifluoromethyl)pyridine as a clear oil, 1.072 g (70%).

後処理

  1. temperatureto cool to room temperature
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with toluene (5 mL)
  4. washThe combined organic phases were washed with water and brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customEvaporation of the solvent
  8. waitleft a brown oil that
  9. customwas chromatographed over silica gel (petroleum ether/ethyl acetate, 9:1)

出典と根拠

ORDレコード
ord-6bab21e86d3a41eb84ffbded31c6ce62
出典データセット
uspto-grants-2013_09
特許番号
US08536203B2

反応ノート

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