Dichloromethane → HCID 67494171, compound

HRID 2047019Notes

Reaction equation

HRID 2047019 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3](B(O)O)[CH:2]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl.[CH3:25][O:26][C:27]([CH:29]1[CH2:34][CH2:33][CH:32]([C:35]2[CH:40]=[C:39]([N:41]([CH2:50][O:51][CH2:52][CH2:53][Si:54]([CH3:57])([CH3:56])[CH3:55])[CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[N:38]3[N:58]=[CH:59][C:60](I)=[C:37]3[N:36]=2)[CH2:31][CH2:30]1)=[O:28]>O1CCOCC1.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]>[CH3:25][O:26][C:27]([CH:29]1[CH2:30][CH2:31][CH:32]([C:35]2[CH:40]=[C:39]([N:41]([CH2:50][O:51][CH2:52][CH2:53][Si:54]([CH3:57])([CH3:56])[CH3:55])[CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:48])([CH3:49])[CH3:47])[N:38]3[N:58]=[CH:59][C:60]([C:3]4[CH:2]=[N:1][C:10]5[C:5]([CH:4]=4)=[CH:6][CH:7]=[CH:8][CH:9]=5)=[C:37]3[N:36]=2)[CH2:33][CH2:34]1)=[O:28]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 2734663Quinoline-3-boronic acidHCID 667384164-{7-[Bis-(2-trimethylsilanyl-ethoxymethyl)-amino]-3-iodo-pyrazolo[1,5-a]pyrimidin-5-yl}-cyclohexanecarboxylic acid methyl ester

Product 1

HCID 67494171HCID 67494171, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

3-Quinoline boronic acid (2.42 mmol, 420 mg), K3PO4 (3.63 mmol, 771 mg), and PdCl2(dppf).CH2Cl2 (0.121 mmol, 100 mg) was added to a solution of 4-{7-[Bis-(2-trimethylsilanyl-ethoxymethyl)-amino]-3-iodo-pyrazolo[1,5-a]pyrimidin-5-yl}-cyclohexanecarboxylic acid methyl ester (1.21 mmol, 800 mg) in dioxane (10 mL). To this suspension was added distilled H2O (1.0 mL). The resulting reaction mixture was stirred at 100° C. under an argon atmosphere for 18 hours. The reaction mixture was concentrated in vacuo and then purified via silica gel chromatography (0% to 60% ethyl acetate in hexanes gradient) to yield the title compound (630 mg, 79% yield) as yellow oil. LC-MS: 662 [M+H].

Workup

  1. additionTo this suspension was added
  2. distillationdistilled H2O (1.0 mL)
  3. customThe resulting reaction mixture
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. custompurified via silica gel chromatography (0% to 60% ethyl acetate in hexanes gradient)

Sources & evidence

ORD record
ord-2f61f20165444c188f952dd4484260cf
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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