Tri-o-tolylphosphine → HCID 16659982, 화합물

HRID 2097068노트

반응식

HRID 2097068 반응식
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

참가 물질

8

반응물 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

생성물 1

HCID 16659982HCID 16659982, 화합물수율 20.3%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 7854Propionitrile용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-c7fd5c823d584a6d86445faf21d1fe85
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450307B2

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