Sodium Carbonate → N-(2-Amino-6-phenyl-4-pyrimidinyl)-N-[3-fluoro-4-(1H-indazol-5-yloxy)phenyl]amine

HRID 16438Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][N:20]=[CH:19]4)=[C:11]([F:25])[CH:10]=2)[CH:5]=[C:4](Cl)[N:3]=1.[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][N:20]=[CH:19]4)=[C:11]([F:25])[CH:10]=2)[CH:5]=[C:4]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

50 mg (130 μmol) of N-[2-amino-6-chloro-4-pyrimidinyl]-N-[3-fluoro-4-(1H-indazol-5-yloxy)phenyl]amine (from example 8) are suspended in 3 ml of toluene/ethanol (2:1), and 4.68 mg of tetrakis(triphenylphosphine)palladium(0) are added. After addition of 19.7 mg (160 μmol) of phenylboronic acid and 0.50 ml of 2M aqueous sodium carbonate solution, the mixture is stirred at 100° C. overnight. The mixture is evaporated to dryness using a rotary evaporator and purified by preparative HPLC.

Workup

customThe mixture is evaporated to dryness
customa rotary evaporator
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-6e17ee2d1ec944e4b2706873a06f98cc
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737153B2

Reaction notes

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