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Tri-o-tolylphosphine → (E)-N-Methyl-N-(3-methylbenzofuran-2-ylmethyl)-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide

HRID 1362331
ノート
印刷プレビュー

反応式

HRID 1362331 の反応式
Cl.Br[C:3]1[CH:14]=[N:13][C:6]2[NH:7][C:8](=[O:12])[CH2:9][NH:10][CH2:11][C:5]=2[CH:4]=1.[CH3:15][N:16]([CH2:21][C:22]1[O:23][C:24]2[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=2[C:26]=1[CH3:27])[C:17](=[O:20])[CH:18]=[CH2:19].C(N(C(C)C)C(C)C)C.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)CC.CN(C=O)C.C(Cl)Cl.CO.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:15][N:16]([CH2:21][C:22]1[O:23][C:24]2[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=2[C:26]=1[CH3:27])[C:17](=[O:20])/[CH:18]=[CH:19]/[C:3]1[CH:14]=[N:13][C:6]2[NH:7][C:8](=[O:12])[CH2:9][NH:10][CH2:11][C:5]=2[CH:4]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 57742103N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamideHCID 66780871HCID 66780871、化合物

生成物 1

HCID 16659988(E)-N-Methyl-N-(3-methylbenzofuran-2-ylmethyl)-3-(2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide収率 47%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 7854Propionitrile溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

A suspension of 7-bromo-1,3,4,5-tetrahydropyrido[2,3-e][1,4]diazepin-2-one hydrochloride (0.29 g, 1.0 mmol) and N-methyl-N-(3-methylbenzofuran-2-ylmethyl)acrylamide (0.29 g, 1.3 mmol) in propionitrile (5 mL) and DMF (1.3 mL) was de-oxygenated with Ar for 10 min. The mixture was treated with (i-Pr)2EtN (0.56 mL, 3.2 mmol) and was de-oxygenated with Ar for 5 min. Pd(OAc)2 (24 mg, 0.11 mmol) and P(o-tol)3 (64 mg, 0.21 mmol) were added simultaneously, and the mixture was de-oxygenated a third time for 5 min. The mixture was heated to reflux overnight, then allowed to cool. The resulting precipitate was isolated by filtration, dissolved in CH2Cl2/MeOH and the solvent was removed in vacuo. Purification by flash column chromatography (silica gel, CH2Cl2/MeOH, 98:2 to 96:4) gave the title compound (0.18 g, 47%) as a white solid: MS (ESI) m/e 391 (M+H)+.

後処理

  1. waitwas de-oxygenated with Ar for 5 min
  2. customfor 5 min
  3. temperatureThe mixture was heated
  4. temperatureto reflux overnight
  5. temperatureto cool
  6. customThe resulting precipitate was isolated by filtration
  7. customthe solvent was removed in vacuo
  8. customPurification by flash column chromatography (silica gel, CH2Cl2/MeOH, 98:2 to 96:4)

出典と根拠

ORDレコード
ord-810b1cb3c63543c6a6bb1dd0f08174d6
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07879872B2

反応ノート

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