Triethylamine → HCID 66653094, compound

HRID 2171004Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6](I)[CH:7]=1.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([N:22]2[CH:26]=[C:25](B3OC(C)(C)C(C)(C)O3)[CH:24]=[N:23]2)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].O.O.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(N(CC)CC)C>COCCOC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:9]([O:13][C:14]([N:16]1[CH2:17][CH2:18][CH:19]([N:22]2[CH:26]=[C:25]([C:6]3[CH:5]=[N:4][CH:3]=[C:2]([Br:1])[CH:7]=3)[CH:24]=[N:23]2)[CH2:20][CH2:21]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 5.68 g (20.0 mmol) 3-bromo-5-iodo-pyridine, 7.55 g (20.0 mmol) 4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-piperidin-1-carboxylic acid tert-butyl ester (synthesis described in WO 2007/066187) and 8.49 g (40.0 mmol) tri-potassium-phosphate-trihydrate in 40 ml 1,2-dimethoxyethane was heated to 80° C. under nitrogen. Then 421 mg (0.60 mmol) bis-(triphenylphosphine)-palladium(II)-chloride and 50 μl (0.361 mmol) triethylamine were added. The reaction mixture was stirred for 16 hours at 80° C. The reaction mixture was partitioned between THF and saturated sodium chloride solution. The organic phase was dried over sodium sulfate and evaporated. The residue was recrystallized from isopropanol yielding 4-[4-(5-bromo-pyridin-3-yl)-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl-ester as slightly yellow crystals; HPLC-MS (A): 2.41 min, [M+H] 407/409.

Workup

customThe reaction mixture was partitioned between THF and saturated sodium chloride solution
dry with materialThe organic phase was dried over sodium sulfate
customevaporated
customThe residue was recrystallized from isopropanol

Sources & evidence

ORD record: ord-17d8b98318d849b9aebb904652092af6
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051318B2

Reaction notes

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