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Potassium Carbonate → HCID 67338572、化合物

HRID 1045108
ノート
印刷プレビュー

反応式

HRID 1045108 の反応式
Cl[C:2]1[C:3](I)=[CH:4][C:5]2[N:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=2[CH:22]=1.[C:24]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.O1CCOCC1.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.C(#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:24]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:29]=[CH:28][C:27]([C:3]2[CH:2]=[CH:22][C:6]3[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])=[N:9][C:5]=3[CH:4]=2)=[CH:26][CH:25]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 59267806HCID 59267806、化合物2 回

生成物 1

HCID 67338572HCID 67338572、化合物

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
2 回
HCID 6342Acetonitrile溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
150 °C

実験手順

A 2 mL Biotage™ microwave vial was charged with 6-chloro-5-iodo-2-methanesulfonyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazole (Intermediate 5, 49.0 mg, 0.100 mmol), biphenyl-4-boronic acid (24.0 mg, 0.120 mmol) and Pd(PPh3)4 (5.8 mg, 5 mol %) following by dioxane (1.0 mL) and 1M aqueous K2CO3 (120 uL). The resulting suspension was heated in a microwave synthesizer (Biotage Initiator™) at 150° C. for 10 min. The microwave procedure was repeated two more times, before each irradiation additional Pd(PPh3)4 (2.9 mg, 2.5 mol %) was added. The reaction mixture was then diluted with EtOAc (5 mL), filtered and the resulting solution was evaporated to dryness in vacuo to give brown oil. The oil was dissolved in ACN and passed through a Thiol StratoSphere™ SPE cartridge (Polymer Labs). The solvent was evaporated to dryness in vacuo to give crude product as colorless oil which was used in the next step without further purification. LR-MS (API-ES): calculated C26H29ClN2O3SSi 512.1, observed m/e 513.0 (M+H)+, 485.0, 455.0 (Rt 3.91 min).

後処理

  1. filtrationfiltered
  2. customthe resulting solution was evaporated to dryness in vacuo
  3. customto give brown oil
  4. customThe solvent was evaporated to dryness in vacuo
  5. customto give crude product as colorless oil which
  6. customwas used in the next step without further purification

出典と根拠

ORDレコード
ord-7d150d36af5549bdb89536d5de987b22
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08563746B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート