Sodium Bicarbonate → HCID 178478381, compound

HRID 855655

Reaction equation

HRID 855655 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([NH:12][C:13]2[NH:14][N:15]=[C:16]([CH:18]3[CH2:20][CH2:19]3)[CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7](I)[CH:8]=2)[N:3]=1.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O.C1([O-])C=CC=CC=1.[K+].C([O-])(O)=O.[Na+]>CS(C)=O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].ClCCl>[Cl:1][C:2]1[N:11]=[C:10]([NH:12][C:13]2[NH:14][N:15]=[C:16]([CH:18]3[CH2:20][CH2:19]3)[CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[Cl:22])[CH:8]=2)[N:3]=1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 27343222-Chlorophenylboronic acidHCID 23670670Potassium phenoxideHCID 178478383HCID 178478383, compound

Product 1

HCID 178478381HCID 178478381, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

To (2-Chloro-6-iodo-quinazolin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine (100 mg, 0.243 mmol) and 2-chlorophenyl boronic acid (57 mg, 0.364 mmol) in DMSO (5 mL, purged with Ar) was added 1.5M potassium phenolate solution (648 μL, 0.97 mmol) and 1,1′bis(diphenylphosphino)ferrocene palladium chloride, complex with dichloromethane (27 mg) and the solution was heated to 60 C in a sealed tube. After 1 hr, solution was poured into sat. NaHCO3 resulting in a yellow solid that was colleted by filtration. Flash chromatography (1–4% methanol in dichloromethane) to give: 73 mg (63% yield). LCMS m/e: 396.2 (M+H), 394.2 (M−H)

Workup

  1. temperaturethe solution was heated to 60 C in a sealed tube
  2. filtrationthat was colleted by filtration
  3. customFlash chromatography (1–4% methanol in dichloromethane) to give

Sources & evidence

ORD record
ord-345d575cc3c2465ca5fbb3eadb937295
Source dataset
uspto-grants-2007_08
Patent number
US07262200B2

Linked notes

Loading…