Hydrochloric Acid → HCID 86692408, compound

HRID 1748438

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][N:13]=2)[C:10]=1[CH3:11])=[O:5])C.C1(P(C2CCCCC2)C2C=CC=CC=2C2[C:37]([O:38][CH3:39])=[CH:36][CH:35]=CC=2OC)CCCCC1.COCC=CB1OC(C)(C)C(C)(C)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[OH-].[Na+].Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(O)C.O1CCCC1>[CH3:39][O:38][CH2:37]/[CH:36]=[CH:35]/[C:15]1[CH:16]=[CH:17][C:12]([N:9]2[C:10]([CH3:11])=[C:6]([C:4]([OH:3])=[O:5])[CH:7]=[N:8]2)=[N:13][CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Tetrahydrofuran (4 ml) was added to 1-(5-bromopyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (620 mg) described in Reference Example 24(2), palladium (II) acetate (45 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos) (82 mg), 3-methoxy-1-propenylboronic acid pinacol ester (594 μl) and tripotassium phosphate (1.0 g), and stirred at 100° C. for 4.5 hours. Then, water (5 ml), 4N aqueous solution of sodium hydroxide (5 ml) and ethanol (5 ml) were added to the reaction solution and the mixture was stirred at 80° C. for two hours. The reaction solution was acidified by the addition of water and 1N hydrochloric acid aqueous solution, extracted with ethyl acetate and the solvent was evaporated in vacuo. The resulting solid was washed with water to give the titled compound (300 mg) as a white solid.

Workup

stirringthe mixture was stirred at 80° C. for two hours
extractionextracted with ethyl acetate
customthe solvent was evaporated in vacuo
washThe resulting solid was washed with water

Sources & evidence

ORD record: ord-1a573bd2686a4f079c7d88279b015f26
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150555B2

Linked notes

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