Sodium Carbonate → HCID 58442828、化合物

HRID 41649ノート

反応式

HRID 41649 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1Br)=[O:4].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH:20]=[C:21]([C:6]2[S:7][CH:8]=[CH:9][C:5]=2[C:3]([O:2][CH3:1])=[O:4])[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 53302196Methyl 2-bromothiophene-3-carboxylate

生成物 1

HCID 58442828HCID 58442828、化合物収率 92.8%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

2-Bromothiophene-3-carboxylic acid methyl ester (3.0 g, 14.0 mmol, 1.0 eq.), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (4.2 g, 14.0 mmol, 1.0 eq.), THF (150 mL) and Na2CO3 (28 mL, 56 mmol, 4.0 eq.) were combined. The mixture was degassed and purged with nitrogen (3×). PdCl2(PPh3)2 (0.3 g, 0.4 mmol, 0.03 eq.) was added, and the mixture was again degassed and purged with nitrogen (3×), then heated at 80° C. overnight. The mixture was then cooled and the layers were separated. The THF layer was diluted with EtOAc (150 mL), washed with saturated aqueous NaCl (50 mL) and dried over Na2SO4. The material was filtered and applied onto a silica gel column and purified by chromatography with PE/EtOAc (20:1˜10:1) to yield 4-(3-methoxycarbonylthiophen-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid t-butyl ester (4.2 g) as a yellow solid.

後処理

  1. customThe mixture was degassed
  2. custompurged with nitrogen (3×)
  3. customthe mixture was again degassed
  4. custompurged with nitrogen (3×)
  5. temperatureThe mixture was then cooled
  6. customthe layers were separated
  7. additionThe THF layer was diluted with EtOAc (150 mL)
  8. washwashed with saturated aqueous NaCl (50 mL)
  9. dry with materialdried over Na2SO4
  10. filtrationThe material was filtered
  11. custompurified by chromatography with PE/EtOAc (20:1˜10:1)

出典と根拠

ORDレコード
ord-0f5415d5673f48bb96e42e9a3912456f
出典データセット
uspto-grants-2013_09
特許番号
US08530663B2

反応ノート

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