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Tri-o-tolylphosphine → (E)-tert-butyl 6-(3-oxo-3-(pyrrolidin-1-yl) prop-1-en-1-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 2174576
ノート
印刷プレビュー

反応式

HRID 2174576 の反応式
CCN(C(C)C)C(C)C.Br[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH2:17][N:16]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15][CH2:14]2.[N:28]1([C:33](=[O:36])[CH:34]=[CH2:35])[CH2:32][CH2:31][CH2:30][CH2:29]1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)CC.CN(C=O)C>[O:36]=[C:33]([N:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)/[CH:34]=[CH:35]/[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH2:17][N:16]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15][CH2:14]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 1820551-(Pyrrolidin-1-yl)prop-2-en-1-oneHCID 49761184tert-Butyl 6-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate

生成物 1

HCID 89602353(E)-tert-butyl 6-(3-oxo-3-(pyrrolidin-1-yl) prop-1-en-1-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate収率 54%

試薬・触媒・溶媒 1

HCID 86641869DMF propionitrile溶媒

反応条件

温度
110 °C

実験手順

DIPEA (1.44 ml, 8.36 mmol) was added to a solution of 125a (650 mg, 2.09 mmol), 125b (287 mg, 2.29 mmol), Pd-(OAc)2 (46 mg, 0.21 mmol) and P(o-tol)3 (127 mg, 0.42 mmol) in propionitrile/DMF (8 ml/2 ml) and the reaction mixture was purged with nitrogen for 10 minutes, then was heated at 110° C. for 16 h. The progress of the reaction was monitored by TLC. After 16 h of stirring, the mixture was cooled to 20-35° C. and filtered on celite. The filtrate was concentrated and resultant residue diluted with water (30 ml) and extracted with ethyl acetate (2×30 ml). The combined organic layers were washed with brine (30 ml), followed by drying over anhydrous Na2SO4 and filtering. The filtrate was rotary evaporated to get residue which was purified by column chromatography using a mixture of 50% ethyl acetate/pet ether as an eluent to get the desired compound as an off-white solid (400 mg, 54%). 1H NMR (400 MHz, DMSO-d6) δ 7.50 (d, J=6.8 Hz, 2H), 7.41 (d, J=15.7 Hz, 1H), 7.20 (d, J=8.3 Hz, 1H), 6.94 (d, J=15.7 Hz, 1H), 4.56-4.46 (m, 2H), 3.63 (t, J=6.6 Hz, is 2H), 3.55 (t, J=5.9 Hz, 2H), 3.41-3.34 (m, 2H), 2.79 (t, J=5.9 Hz, 2H), 1.96-1.88 (m, 2H); 1.87-1.76 (m, 2H), 1.43 (s, 9H).

後処理

  1. customthe reaction mixture was purged with nitrogen for 10 minutes
  2. temperaturethe mixture was cooled to 20-35° C.
  3. filtrationfiltered on celite
  4. concentrationThe filtrate was concentrated
  5. additionresultant residue diluted with water (30 ml)
  6. extractionextracted with ethyl acetate (2×30 ml)
  7. washThe combined organic layers were washed with brine (30 ml)
  8. dry with materialby drying over anhydrous Na2SO4
  9. filtrationfiltering
  10. customThe filtrate was rotary evaporated
  11. customto get residue which
  12. customwas purified by column chromatography
  13. additiona mixture of 50% ethyl acetate/pet ether as an eluent

出典と根拠

ORDレコード
ord-869ff5d9f521402e960701d25c3abf24
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09062002B2

反応ノート

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