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Potassium Carbonate → 5-(4-(3-Chloro-4-(pyridin-2-ylmethoxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

HRID 877086
Notes
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Reaction equation

HRID 877086 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25](I)[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.[O:29]1[CH:33]=[CH:32][CH:31]=[C:30]1B(O)O.[C:37]([O-])([O-])=[O:38].[K+].[K+]>[Pd].CCO.COCCOC>[Cl:2][C:3]1[CH:4]=[C:5]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:33]4[O:29][C:30]([CH:37]=[O:38])=[CH:31][CH:32]=4)[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2734357Furan-2-boronic acidHCID 68153209[3-Chloro-4-(2-pyridylmethoxyl)-phenyl]-(6-iodo-quinazolin-4-yl)-amine hydrochloride salt

Product 1

HCID 874249045-(4-(3-Chloro-4-(pyridin-2-ylmethoxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde

Reagents, catalysts & solvents 3

HCID 23938
Palladium
Catalyst
HCID 702EthanolSolvent
HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of compound 8.3 (489 mg, 1.0 mmol), 2-furylboronic acid (185 mg, 1.2 mmol) and palladium catalyst (73.0 mg, 0.10 mmol) in 1.0 mL of K2CO3 (2.0M), 1.0 mL of EtOH and 4.0 mL of DME was heated at 75° C. under nitrogen atmosphere for 4 hr. LS-MS showed the reaction completed. Concentrated the mixture under reduced pressure and washed the residue with water (2×5.0 mL) then with cool ether (10.0 mL) to get a gray solid (400 mg), which was used for next step without further purification.

Workup

  1. concentrationConcentrated the mixture under reduced pressure
  2. washwashed the residue with water (2×5.0 mL)

Sources & evidence

ORD record
ord-ae9d60f09a4f4ad2a023ef63d479a528
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08987284B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes