Potassium Carbonate → HCID 59370348, compound

HRID 661635Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:33])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]([C:15](=[O:32])[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18](B2OC(C)(C)C(C)(C)O2)[CH:17]=1)[CH3:14].Br[C:35]1[CH:36]=[CH:37][C:38]([Cl:41])=[N:39][CH:40]=1.[C:42]([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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>[CH3:1][O:2][C:3](=[O:33])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]([C:15](=[O:32])[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([C:35]2[CH:40]=[N:39][C:38]([Cl:41])=[CH:37][C:36]=2[CH3:42])[CH:17]=1)[CH3:14]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-(2-{[4-chloro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoyl]-methyl-amino}-phenyl)-butyric acid methyl ester (50 mg, 0.11 mmol), 5-bromo-2-chloro-pyridine (26 mg, 0.13 mmol), Pd(PPh3)4 (6 mg, 0.005 mmol), K2CO3 (36 mg, 0.18 mmol) in dioxane (0.6 mL), was heated at 100° C. for 12 hrs. The mixture was purified after a filtration by prep. LCMS to yield 4-(2-{[4-chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-benzoyl]-methyl-amino}-phenyl)-butyric acid methyl ester 13-1. MS [M+H]+: 470.9; tR=8.41 min. (method 2).

Workup

customThe mixture was purified
filtrationafter a filtration by prep

Sources & evidence

ORD record: ord-121f19c66c0a49b3854e81d573ae7403
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084614B2

Reaction notes

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