Potassium Carbonate → HCID 86610197, compound

HRID 1993973Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]#[N:11])=[CH:4][CH:3]=1.[CH3:12][N:13]1[C:17]([C:18]#[N:19])=[CH:16][CH:15]=[C:14]1B(O)O.C(=O)([O-])[O-].[K+].[K+].COC(OC)COCC(OC)OC.O>O>[C:18]([C:17]1[N:13]([CH3:12])[C:14]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]#[N:11])=[CH:4][CH:3]=2)=[CH:15][CH:16]=1)#[N:19]

Participants

Conditions

Temperature: 10 °C

Procedure

(4-bromophenyl)methyl cyanamide (0.100 g, 0.47 mmol) tetrakis(triphenylphosphine)palladium(0) (0.050 g, 0.043 mmol), N-methyl-5-cyanopyrroleboronic acid (0.150 g, 1 mmol), potassium carbonate (0.345 g, 2.5 mmol) and dimethoxyethylether/water 3:1 were placed in a microwave reaction vial fitted with a septa. The vial was then filled with a continuous flow of nitrogen. Using microwave assisted conditions, the mixture was heated to 10° C. for 15 minutes. The mixture was poured into water, extracted with ethyl acetate, the ethylacetate dried over magnesium sulfate, and evaporated in vacuo. The residue was flash chromatographed using 9/1 Hexane/ethylacetate to give [4-(5-cyano-1-methyl-1H-pyrrol-2-yl)phenyl]methylcyanamide (0.030 g, 27%). HPLC purity 100% at 210-370 nm, 10 min.; the Xterra™ RP18 instrument, 3.5μ, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (Ammon. Form. Buff. Ph=3.5/ACN+MeOH) for 10 min., hold 4 min. HRMS: calcd for C14H12N4+H+, 237.11347; found (ESI, [M+H]+), 237.1127.

Workup

customvial fitted with a septa
additionThe vial was then filled with a continuous flow of nitrogen
extractionextracted with ethyl acetate
dry with materialthe ethylacetate dried over magnesium sulfate
customevaporated in vacuo
customchromatographed

Sources & evidence

ORD record: ord-16f77ce8eeb743658628d38ce90c73c9
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652062B2

Reaction notes

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