Tri-o-tolylphosphine → HCID 16659982、化合物

HRID 2097068ノート

反応式

HRID 2097068 の反応式
Br[C:2]1[CH:15]=[N:14][C:5]2[NH:6][C:7](=[O:13])[C:8]([CH3:12])([CH3:11])[NH:9][CH2:10][C:4]=2[CH:3]=1.[CH2:16]([C:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[O:20][C:19]=1[CH2:27][N:28]([CH3:33])[C:29](=[O:32])[CH:30]=[CH2:31])[CH3:17].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.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:11][C:8]1([CH3:12])[C:7](=[O:13])[NH:6][C:5]2[N:14]=[CH:15][C:2](/[CH:31]=[CH:30]/[C:29]([N:28]([CH2:27][C:19]3[O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:18]=3[CH2:16][CH3:17])[CH3:33])=[O:32])=[CH:3][C:4]=2[CH2:10][NH:9]1

参加物

8

反応物 4

HCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 59277547N-(3-ethyl-benzofuran-2-ylmethyl)-N-methylacrylamideHCID 594569147-Bromo-3,3-dimethyl-1,3,4,5-tetrahydropyrido[2,3-e][1,4]diazepin-2-one

生成物 1

HCID 16659982HCID 16659982、化合物収率 20.3%

試薬・触媒・溶媒 3

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

実験手順

To 7-bromo-3,3-dimethyl-1,3,4,5-tetrahydro-pyrido[2,3-e][1,4]diazepin-2-one (400 mg, 1.48 mmol) in propionitrile (40 mL) and DMF (10 mL) was added N-(3-ethyl-benzofuran-2-ylmethyl)-N-methylacrylamide (410 mg, 1.62 mmol), (i-Pr)2EtN (0.51 mL, 2.96 mmol), Pd(OAc)2 (332 mg, 0.148 mmol) and P(o-tol)3 (90.1 mg, 0.296 mmol), and the mixture was de-oxygenated with argon for 15 min. The mixture was heated to reflux overnight, allowed to cool and then filtered. The filtrate was concentrated and the residue was dissolved in CH2Cl2 (150 mL). The organic solution was washed with water and brine, dried (Na2SO4) and the solvent was removed in vacuo. Purification by column chromatography (silica gel, CH2Cl2/MeOH, 20:1) gave the title compound (130 mg, 20%) as an off-white solid: MS m/z 433 (M+H)+.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. temperatureto cool
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. dissolutionthe residue was dissolved in CH2Cl2 (150 mL)
  7. washThe organic solution was washed with water and brine
  8. dry with materialdried (Na2SO4)
  9. customthe solvent was removed in vacuo
  10. customPurification by column chromatography (silica gel, CH2Cl2/MeOH, 20:1)

出典と根拠

ORDレコード
ord-c7fd5c823d584a6d86445faf21d1fe85
出典データセット
uspto-grants-2013_05
特許番号
US08450307B2

反応ノート

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