Furan → HCID 15480239、化合物

HRID 1780299ノート

反応式

HRID 1780299 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C([Li])(CC)C.B(OC)(OC)OC.C(=O)([O-])[O-].[Na+].[Na+].Br[C:25]1[CH:26]=[C:27]([O:31][CH2:32][C@@H:33]2[CH2:37][CH2:36][CH2:35][N:34]2[CH3:38])[CH:28]=[N:29][CH:30]=1.C(=O)(O)[O-].[Na+]>C1COCC1.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.O.C1C=CC=CC=1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:25]1[CH:26]=[C:27]([O:31][CH2:32][C@@H:33]2[CH2:37][CH2:36][CH2:35][N:34]2[CH3:38])[CH:28]=[N:29][CH:30]=1

参加物

11

反応物 6

HCID 8029FuranHCID 8470Trimethyl borateHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 112887213-Bromo-5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridineHCID 178418400CID 53628100

生成物 1

HCID 15480239HCID 15480239、化合物収率 99%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 241Benzene溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of furan (1.45 mL, 20.0 mmol) in THF (30.0 mL) was added sec-butyllithium (1.3M, 7.69 mL, 10.0 mmol) at -78° C. After half an hour at this temperature, trimethyl borate (2.27 mL, 20.0 mmol) was added. The reaction mixture was stirred at -78° C. for one hour and slowly warmed up to room temperature. Solvent was removed, and benzene (10.0 mL), sodium carbonate (2.0M, 5.0 mL), tetrakis(triphenylphosphine)palladium(0) (175 mg) and 5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine (1.36 g, 5.0 mmol) were added. The reaction mixture was refluxed overnight, then cooled to room temperature. Water (2 mL) was added, and solid sodium bicarbonate was added until the aqueous layer was saturated. The mixture was extracted with EtOAc, which was dried over MgSO4, filtered and concentrated. The residue was chromatographed on a silica gel column, eluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90 to afford an oil (1.27 g, 99%). MS (CI/NH3) m/z 259 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.70-2.22 (m, 4H), 2.28-2.40 (m, 1H), 2.51 (s, 3H), 2.66-2.75 (m, 1H), 3.10-3.18 (m, 1H), 3.97-4.11 (m, 2H), 6.51 (dd, J=4.8 Hz, J=3.6 Hz, 1H), 6.74 (d, J=4.9 Hz, 1H), 7.47 (dd, J=3.0 Hz, J=2.1 Hz, 1H), 7.53 (d, J=3.6 Hz, 1H), 8.22 (d, J=3.0 Hz, 1H), 8.54 (d, J=2.1 Hz, 1H).

後処理

  1. temperatureslowly warmed up to room temperature
  2. customSolvent was removed
  3. temperatureThe reaction mixture was refluxed overnight
  4. temperaturecooled to room temperature
  5. extractionThe mixture was extracted with EtOAc, which
  6. dry with materialwas dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was chromatographed on a silica gel column
  10. washeluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90

出典と根拠

ORDレコード
ord-c1ea9d07f34d4617901ea43ab1609779
出典データセット
uspto-grants-1997_05
特許番号
US05629325

反応ノート

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