Potassium Phosphate, Tribasic → [7-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-carbamic acid tert-butyl ester

HRID 626714노트

반응식

HRID 626714 반응식
Br[C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=[C:6]2[C:5]([Cl:19])=[CH:4][N:3]=1.[C:20](=[O:27])([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[NH2:21].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.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].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>[C:23]([O:22][C:20](=[O:27])[NH:21][C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=[C:6]2[C:5]([Cl:19])=[CH:4][N:3]=1)([CH3:26])([CH3:25])[CH3:24]

참가 물질

8

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 77922tert-Butyl carbamateHCID 866970524bromo-7-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

생성물 1

HCID 69671401[7-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-carbamic acid tert-butyl ester수율 121.1%

시약·촉매·용매 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
70 °C

실험 절차

A mixture of 4-bromo-7-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (400 mg, 1.06 mmol), tert-butyl carbamate (619 mg, 5.3 mmol), Pd2(dba)3 (48 mg, 0.05 mmol), Xantphos (61 mg, 0.1 mmol) and potassium phosphate tribasic (449 mg, 2.1 mmol) in toluene (10 mL) and water (2.0 mL) was purged with argon and heated at 70° C. for 3 hours. The reaction mixture was filtered through Celite® and washed with ethyl acetate. The filtrate was washed with water and brine, dried over sodium sulphate, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-50% ethyl acetate in cyclohexane) to afford the title compound as a yellow solid (531 mg, contaminated with residual tert-butyl carbamate). LCMS (Method D): RT=3.76 min, m/z: 413 [M+H+].

후처리

  1. customwas purged with argon
  2. filtrationThe reaction mixture was filtered through Celite®
  3. washwashed with ethyl acetate
  4. washThe filtrate was washed with water and brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel flash chromatography (0-50% ethyl acetate in cyclohexane)

출처 및 근거

ORD 기록
ord-7e5aa8b72fd442cb9d42801777fb2e1e
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

반응 노트

불러오는 중…