Sodium Carbonate → HCID 59579974, compound

HRID 2279659Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([CH2:13][NH:14][C:15]([C:17]3[S:21][C:20](Br)=[N:19][C:18]=3[C:23]([F:26])([F:25])[F:24])=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:2]=1.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][N:30]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.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>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([CH2:13][NH:14][C:15]([C:17]3[S:21][C:20]([C:32]4[CH:31]=[N:30][C:29]([O:28][CH3:27])=[CH:34][CH:33]=4)=[N:19][C:18]=3[C:23]([F:26])([F:25])[F:24])=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:2]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-bromo-4-trifluoromethyl-thiazole-5-carboxylic acid (1-pyridin-3-yl-cyclohexylmethyl)-amide (44.8 mg), 2-methoxy-5-pyridineboronic acid (30.6 mg), Pd(PPh3)4 (5.8 mg) and Na2CO3 (42.4 mg) in dioxane (2 mL) and water (0.8 mL) is heated at 110° C. in an argon purged sealed vial for 2 h. The mixture is poured into water and extracted with EtOAc. The extract is concentrated and the residue is purified by PTLC (silica gel, 5% MeOH in methylene chloride) to give the title compound. MS (M+1)=477.19; RT=1.19 min. *IC50.

Workup

custompurged
customsealed vial for 2 h
additionThe mixture is poured into water
extractionextracted with EtOAc
concentrationThe extract is concentrated
customthe residue is purified by PTLC (silica gel, 5% MeOH in methylene chloride)

Sources & evidence

ORD record: ord-900fddb485d14bed8bb8690d5a34e856
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133204B2

Reaction notes

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