Triethylamine → 1-(3,4-Methylenedioxyphenyl)-2-[5-(3-pyridinyl)-pyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-beta-carboline

HRID 2415386ノート

反応式

HRID 2415386 の反応式
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23]3[N:28]=[CH:27][C:26](Br)=[CH:25][N:24]=3)=[CH:4][C:3]=2[O:2]1.[N:30]1[CH:35]=[CH:34][CH:33]=[C:32](B(O)O)[CH:31]=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23]3[N:28]=[CH:27][C:26]([C:32]4[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=4)=[CH:25][N:24]=3)=[CH:4][C:3]=2[O:2]1

参加物

8

反応物 3

HCID 8471TriethylamineHCID 27343783-Pyridinylboronic acidHCID 226403241-(3,4-Methylenedioxyphenyl)-2-(5-bromopyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-beta-carboline

生成物 1

HCID 226403091-(3,4-Methylenedioxyphenyl)-2-[5-(3-pyridinyl)-pyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-beta-carboline

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

A stirred mixture of palladium(II) acetate (27 mg, 0.12 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (dppf) (83 mg, 0.15 mmol) in dry DMF (20 ml) was warmed to 50° C. for 15 min and then cooled. 1-(3,4-methylenedioxyphenyl)-2-(5-bromopyrimidin-2-yl)-2,3,4,9-tetrahydro-1H-β-carboline (674 mg, 1.5 mmol) (prepared as in Example 52), pyridine-3-boronic acid (203 mg, 1.7 mmol) and triethylamine (0.3 ml, 2.1 mmol) were added to the solution and the mixture heated to 90° C. for 16 h. The solution was diluted with ethyl acetate and filtered through filter paper. The organic phase was washed with brine and water, then dried over Na2SO4. A small amount of silica gel was added into the solution and the solution was dried in vacuo. Purification by flash column (silica gel, hexane:ethyl acetate=1:1, v/v, followed by hexane:ethyl acetate=1:2, v/v) yielded the product as a white solid.

後処理

  1. temperaturecooled
  2. temperaturethe mixture heated to 90° C. for 16 h
  3. filtrationfiltered
  4. filtrationthrough filter paper
  5. washThe organic phase was washed with brine and water
  6. dry with materialdried over Na2SO4
  7. additionA small amount of silica gel was added into the solution
  8. customthe solution was dried in vacuo
  9. customPurification by flash column (silica gel, hexane

出典と根拠

ORDレコード
ord-bd0841c0531c4ad79efe97d063a0f527
出典データセット
uspto-grants-2004_11
特許番号
US06818646B2

反応ノート

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