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 2047122Notes

Reaction equation

HRID 2047122 reaction equation
[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

Participants

6

Reactant 3

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

Product 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

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3ac85d4a187e4bf9875711ec3f227c5e
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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