Potassium Carbonate → HCID 68797031, compound

HRID 869963Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]([C:11]2([C:14]3[CH:24]=[CH:23][C:17]4[O:18][C:19]([F:22])([F:21])[O:20][C:16]=4[CH:15]=3)[CH2:13][CH2:12]2)=[O:10])[CH:5]=[C:4]([CH3:25])[C:3]=1[C:26]#[N:27].C(=O)([O-])[O-].[K+].[K+].[CH3:34][O:35][C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][N:37]=1>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.COCCOC>[C:26]([C:3]1[C:2]([C:39]2[CH:38]=[N:37][C:36]([O:35][CH3:34])=[CH:41][CH:40]=2)=[N:7][C:6]([NH:8][C:9]([C:11]2([C:14]3[CH:24]=[CH:23][C:17]4[O:18][C:19]([F:21])([F:22])[O:20][C:16]=4[CH:15]=3)[CH2:12][CH2:13]2)=[O:10])=[CH:5][C:4]=1[CH3:25])#[N:27]

Participants

Conditions

Temperature: 80 °C

Procedure

N-(6-chloro-5-cyano-4-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (369 mg, 0.94 mmol), potassium carbonate (1.45 g, 942.0 μL of 2 M, 1.88 mmol), tetrakis(triphenylphosphine)palladium (0) (54 mg, 0.047 mmol), 1,2-dimethoxyethane (9 mL), and 2-methoxypyridine-5-boronic acid (230.5 mg, 1.51 mmol) were combined in a 40 mL scintillation vial. The reaction mixture was heated to 80° C. for 6 hours. The reaction mixture was allowed to cool to room temperature, the layers were separated, and the crude material was purified on 40 g of silica gel utilizing a gradient of 0-80% ethyl acetate in hexanes to yield the pure product (0.437 g, 71%). ESI-MS m/z calc. 464.1. found 465.1 (M+1)+. Retention time 2.08 minutes.

Workup

temperatureto cool to room temperature
customthe layers were separated
customthe crude material was purified on 40 g of silica gel utilizing a gradient of 0-80% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-cd4c77ab916f49cdaf6ea789277ee953
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969386B2

Reaction notes

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