1-tert-Butyl-4-iodobenzene → HCID 58032084、化合物

HRID 1429275

反応式

HRID 1429275 の反応式
[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.[C:19]([C:23]1[CH:28]=[CH:27][C:26](I)=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20].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>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].C(#N)C.O.ClCCl>[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:26]3[CH:27]=[CH:28][C:23]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:24][CH:25]=3)[CH2:11]2)[CH:5]=[CH:6][CH:7]=1

参加物

10

反応物 4

HCID 1420291-tert-Butyl-4-iodobenzeneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 45749132-Methylpropan-2-olateHCID 66630367HCID 66630367、化合物

生成物 1

HCID 58032084HCID 58032084、化合物収率 31.9%

試薬・触媒・溶媒 5

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

A mixture of 3,3-bis(3-bromophenyl)azetidine (60 mg, 0.163 mmol), 1-tert-butyl-4-iodobenzene (85 mg, 0.327 mmol), xantphos (9.46 mg, 0.016 mmol), Pd2(dba)3 (3.74 mg, 4.09 μmol) and tert-butoxide (18.85 mg, 0.196 mmol) in dioxane (5 mL) was stirred at 110° C. for 12 h. After the reaction was cooled to room temperature, water (15 mL) and dichloromethane (15 mL) was added. The aqueous phase was extracted with dichloromethane (15 mL×3). The combined organic layers were dried and concentrated. The residue was purified by prep-HPLC (Instrument waters 2767 PHW004 Column YMC-Triart C18 150*20 mm S-5 um 12 nm Mobile Phase A: water (0.05% NH4HCO3) B: ACN Gradient 95-95% B in 8 min stop in 14 min Flow Rate(ml/min) 20.00 Detective Wavalength(nm) 214\254 Retention Time(min) 7.4 to afford 26 mg of the title compound (0.052 mmol, 31.8% yield). LC/MS: [M+1]=500.

後処理

  1. temperatureAfter the reaction was cooled to room temperature
  2. extractionThe aqueous phase was extracted with dichloromethane (15 mL×3)
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customThe residue was purified by prep-HPLC (Instrument waters 2767 PHW004 Column YMC-Triart C18 150*20 mm S-5 um 12 nm Mobile Phase A

出典と根拠

ORDレコード
ord-644f95dd1d5b43aabb437acccb4f36e5
出典データセット
uspto-grants-2015_01
特許番号
US08937150B2

関連ノート

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