Potassium Carbonate → 2-(4-(5-(Methoxymethyl)pyridine-3-yl)phenyl)-2-methylpropanoic acid

HRID 1175605ノート

反応式

HRID 1175605 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH2:8][O:9][CH3:10])[CH:7]=1.B([C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:25])([CH3:24])[C:21]([OH:23])=[O:22])=[CH:16][CH:15]=1)(O)O.C([O-])([O-])=O.[K+].[K+]>COCCOC.O.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>[CH3:10][O:9][CH2:8][C:6]1[CH:7]=[C:2]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:25])([CH3:24])[C:21]([OH:23])=[O:22])=[CH:16][CH:15]=2)[CH:3]=[N:4][CH:5]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 186245693-Bromo-5-(methoxymethyl)pyridineHCID 509991372-(4-Boronophenyl)-2-methylpropanoic acid

生成物 1

HCID 687744252-(4-(5-(Methoxymethyl)pyridine-3-yl)phenyl)-2-methylpropanoic acid収率 88%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

3-bromo-5-(methoxymethyl)pyridine (example 32b) (4.8 g, 23.56 mmol), 2-(4-boronophenyl)-2-methylpropanoic acid (example 21b) (5.4 g, 25.92 mmol) and K2CO3 (6.5 g, 47.12 mmol) were mixed in DME (60 mL) and 15 ml of water (15 mL). The mixture was degassed for 30 minutes and Pd(PPh3)4 (0.55 g, 0.47 mmol) was added. The reaction mixture was heated to reflux for 16 hr then cooled to room temperature, and evaporated under reduced pressure. The residue was diluted with aqueous NaOH (0.5 N, 60 mL) and stirred for 30 min., and the solution extracted with ether (20 mL×3). The aqueous phase was cooled to 0° C., acidified with 2 N HCl to PH=5˜6, then extracted with EtOAc. The organic phase was washed successively with water and brine, dried over MgSO4, filtered and evaporated. The residue was triturated with hexane, filtered and evaporated to give 5.9 g of 2-(4-(5-(methoxymethyl)pyridine-3-yl)phenyl)-2-methylpropanoic acid as a light brown solid in 88% yield. 1H NMR (400 MHz, CDCl3): δ 1.66 (s, 6H), 3.44 (s, 3H), 4.54 (s, 2H), 7.54-7.56 (d, 4H), 7.92 (s, 1H), 8.56 (s, 1H), 8.76 (s, 1H). MS (M+H, 286).

後処理

  1. customThe mixture was degassed for 30 minutes
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 16 hr
  4. customevaporated under reduced pressure
  5. additionThe residue was diluted with aqueous NaOH (0.5 N, 60 mL)
  6. extractionthe solution extracted with ether (20 mL×3)
  7. temperatureThe aqueous phase was cooled to 0° C.
  8. extractionextracted with EtOAc
  9. washThe organic phase was washed successively with water and brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. customevaporated
  13. customThe residue was triturated with hexane
  14. filtrationfiltered
  15. customevaporated

出典と根拠

ORDレコード
ord-fdbf00f816aa403cbb6cb840cb56b0ee
出典データセット
uspto-grants-2010_11
特許番号
US07842324B2

反応ノート

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