Sodium Bicarbonate → HCID 86640496, 화합물

HRID 561029노트

반응식

HRID 561029 반응식
[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]

참가 물질

7

반응물 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

생성물 1

HCID 86640496HCID 86640496, 화합물수율 100%

시약·촉매·용매 3

HCID 24290Palladium Chloride촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
85 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-1344b220f4cb41ff8c7a934d0ab9a197
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063212B2

반응 노트

불러오는 중…