Iodobenzene → 3,3-Bis(3-bromophenyl)-1-phenylazetidine

HRID 1429276노트

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HRID 1429276 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=3)[CH2:11][NH:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.I[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].ClCCl.O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=3)[CH2:9][N:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:11]2)[CH:5]=[CH:6][CH:7]=1

참가 물질

9

반응물 4

HCID 11575IodobenzeneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 666303673,3-Bis(3-bromophenyl)azetidine

생성물 1

HCID 580320243,3-Bis(3-bromophenyl)-1-phenylazetidine수율 58%

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A mixture of 3,3-bis(3-bromophenyl)azetidine (200 mg, 0.545 mmol), iodobenzene (222 mg, 1.090 mmol), xantphos (31.5 mg, 0.054 mmol), Pd2(dba)3 (12.47 mg, 0.014 mmol) and sodium tert-butoxide (62.8 mg, 0.654 mmol) in dioxane (3 ml) was stirred for 12 h at 100° C. After cooling to room temperature, water (15 mL) and dichloromethane (15 mL) was added. The aqueous layer was extracted with dichloromethane (15 mL×3). The combined organic layers were dried and concentrated. The residue was purified by prep-TLC (eluent with dichloromethane: EtOAc=5:1) to afford 140 mg of the title compound (0.31 mmol, 58%). LC/MS: [M+1]=444, Ret. Time: 2.69 min. 1HNMR (CDCl3), 400 MHz: 4.42 (s, 4H), 6.54 (d, 2H, J=7.6 Hz), 7.09-7.11 (m, 2H), 6.79 (t, 1H, J=7.2 Hz), 7.17-7.26 (m, 6H), 7.37-7.45 (m, 4H).

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionThe aqueous layer was extracted with dichloromethane (15 mL×3)
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customThe residue was purified by prep-TLC (eluent with dichloromethane: EtOAc=5:1)

출처 및 근거

ORD 기록
ord-cbe28636128e4699ae7b586b4a15ff96
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08937150B2

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