Potassium Phosphate, Tribasic → Tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidine-1-carboxylate

HRID 2047122노트

반응식

HRID 2047122 반응식
[CH3:1][Si:2]([CH3:39])([CH3:38])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:8]1[N:13]2[N:14]=[CH:15][C:16](I)=[C:12]2[N:11]=[C:10]([CH:18]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19]2)[CH:9]=1.[N:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[C:42](B(O)O)[CH:41]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:1][Si:2]([CH3:39])([CH3:38])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:42]3[CH:41]=[N:40][C:49]4[C:44]([CH:43]=3)=[CH:45][CH:46]=[CH:47][CH:48]=4)=[C:12]2[N:11]=[C:10]([CH:18]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19]2)[CH:9]=1

참가 물질

6

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 2734663Quinoline-3-boronic acidHCID 67494509HCID 67494509, 화합물

생성물 1

HCID 67494694Tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidine-1-carboxylate

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
100 °C

실험 절차

A mixture of tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidine-1-carboxylate (703 mol), quinolin-3-ylboronic acid (350 mg, 2.00 mmol), Pd(dppf)Cl2—CH2Cl2 (82 mg, 0.10 mmol) and potassium phosphate (636 mg, 3.0 mmol) in a mixture of dioxane/H2O (9:1, 20 mL) was heated at 100° C. for 5 h under argon. The reaction mixture was cooled down and diluted with EtOAC, washed with Brine, dried over Na2SO4, filtered and concentrated. The residue was purified by Biotage (CH2Cl2/EtOAc, 10:1 to 3:1) to give the title compound as brown solid. LC/MS RT=2.49 min. Mass calculated for, M+H 690.37, observed 389.17.

후처리

  1. temperatureThe reaction mixture was cooled down
  2. additiondiluted with EtOAC
  3. washwashed with Brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by Biotage (CH2Cl2/EtOAc, 10:1 to 3:1)

출처 및 근거

ORD 기록
ord-3ac85d4a187e4bf9875711ec3f227c5e
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08591943B2

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