Sodium Bicarbonate → HCID 86640496、化合物

HRID 561029ノート

反応式

HRID 561029 の反応式
[N:1]([CH2:4][C:5]1[C:6](I)=[CH:7][C:8]([F:11])=[N:9][CH:10]=1)=[N+:2]=[N-:3].[F:13][C:14]1[C:15]([C:29]2[S:33][C:32]3[C:34](B4OC(C)(C)C(C)(C)O4)=[CH:35][CH:36]=[CH:37][C:31]=3[CH:30]=2)=[N:16][C:17]([NH:20][CH2:21][CH2:22][N:23]2[CH2:27][CH2:26][NH:25][C:24]2=[O:28])=[N:18][CH:19]=1.C([O-])(O)=O.[Na+]>CS(C)=O.O.Cl[Pd]Cl>[N:1]([CH2:4][C:5]1[C:6]([C:34]2[C:32]3[S:33][C:29]([C:15]4[C:14]([F:13])=[CH:19][N:18]=[C:17]([NH:20][CH2:21][CH2:22][N:23]5[CH2:27][CH2:26][NH:25][C:24]5=[O:28])[N:16]=4)=[CH:30][C:31]=3[CH:37]=[CH:36][CH:35]=2)=[CH:7][C:8]([F:11])=[N:9][CH:10]=1)=[N+:2]=[N-:3]

参加物

7

反応物 3

HCID 516892Sodium BicarbonateHCID 666734811-(2-{5-Fluoro-4-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[b]thiophen-2-yl]-pyrimidin-2-ylamino}-ethyl)-imidazolidin-2-oneHCID 866404905-Azidomethyl-2-fluoro-4-iodo-pyridine

生成物 1

HCID 86640496HCID 86640496、化合物収率 100%

試薬・触媒・溶媒 3

HCID 24290Palladium Chloride触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
85 °C

実験手順

Combine 5-azidomethyl-2-fluoro-4-iodo-pyridine (70 mg, 0.25 mmol) and 1-(2-{5-fluoro-4-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[b]thiophen-2-yl]-pyrimidin-2-ylamino}-ethyl)-imidazolidin-2-one (100 mg, 0.21 mmol) bis(diphenylphosphino)ferrocene)dichloro palladium (8.5 mg, 0.01 mmol) and NaHCO3 (35 mg, 0.41 mmol) in DMSO (87 mL) and water (3 mL). Purge the mixture through nitrogen for 5 min twice. Heat the mixture at 85° C. for 1 hour in an oil bath. Cool to room temperature. Dilute the reaction mixture with chloroform/isopropyl alcohol 93/1), and wash with water and saturated aqueous sodium chloride. Separate the organic layer from the aqueous layer and dry over sodium sulfate. After filtration, remove the organic solvent to give a crude mixture. Purify the crude by column chromatography (10% methanol in dichloromethane) to afford the title compound (105 mg, 100%). MS (ES) m/z 508 [M+1]+.

後処理

  1. customPurge the mixture through nitrogen for 5 min twice
  2. temperatureCool to room temperature
  3. additionDilute the reaction mixture with chloroform/isopropyl alcohol 93/1), and
  4. washwash with water and saturated aqueous sodium chloride
  5. customSeparate the organic layer from the aqueous layer
  6. dry with materialdry over sodium sulfate
  7. filtrationAfter filtration
  8. customremove the organic solvent
  9. customto give a crude mixture
  10. customPurify the crude by column chromatography (10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-1344b220f4cb41ff8c7a934d0ab9a197
出典データセット
uspto-grants-2011_11
特許番号
US08063212B2

反応ノート

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