Sodium Bicarbonate → HCID 178478381, compound

HRID 1176040Notes

Reaction equation

HRID 1176040 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-eba73d1f78184cff80cccd1cc6e7c417
Source dataset
uspto-grants-2010_11
Patent number
US07842712B2

Reaction notes

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