Potassium Carbonate → HCID 44540304, compound

HRID 1695766Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[C:19]1[CH:27]=[C:26]2[C:22]([CH:23]=[N:24][NH:25]2)=[C:21]([NH:28][C:29]([C:31]2[N:32]=[C:33]([CH3:36])[S:34][CH:35]=2)=[O:30])[CH:20]=1>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]>[C:1]([C:3]1[CH:4]=[C:5]([C:19]2[CH:27]=[C:26]3[C:22]([CH:23]=[N:24][NH:25]3)=[C:21]([NH:28][C:29]([C:31]3[N:32]=[C:33]([CH3:36])[S:34][CH:35]=3)=[O:30])[CH:20]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

Conditions

Temperature: 150 °C

Procedure

(3-Cyanophenyl)boronic acid (17 mg, 0.12 mmol), 0.6 M potassium carbonate (aq) (0.2 ml, 0.12 mmol) and Pd(dppf)Cl2 (10 mg, 0.014 mmol) in 1,4-dioxane (1 ml) were treated with N-(6-bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide (40 mg, 0.12 mmol) in 1,4-dioxane (1 ml). The reaction was heated in a CEM Discover microwave at 150° C. for 30 mins. After cooling the solvent was removed in vacuo. The residue was dissolved in MeOH and loaded onto a C18 SPE cartridge eluting with 0.1% TFA in MeCN (3×3 ml). The solvent was removed under a stream of nitrogen. The residue was purified by MDAP (Method C) to give the title compound.

Workup

temperatureAfter cooling the solvent
customwas removed in vacuo
dissolutionThe residue was dissolved in MeOH
washeluting with 0.1% TFA in MeCN (3×3 ml)
customThe solvent was removed under a stream of nitrogen
customThe residue was purified by MDAP (Method C)

Sources & evidence

ORD record: ord-68d7f54d5d7a4e09a1a390bd3d0e1871
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163743B2

Reaction notes

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