Hydrochloric Acid → HCID 44136344, compound

HRID 2363726Notes

Reaction equation

Br.[C:2]1([NH:8][C:9]([C:11]2[N:12]=[C:13]3[CH:18]=[CH:17][C:16]([B:19]4[O:23]C(C)(C)C(C)(C)[O:20]4)=[CH:15][N:14]3[CH:28]=2)=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:29].C1(B(O)O)C=CC=CC=1>C(#N)C>[ClH:29].[C:2]1([NH:8][C:9]([C:11]2[N:12]=[C:13]3[CH:18]=[CH:17][C:16]([B:19]([OH:23])[OH:20])=[CH:15][N:14]3[CH:28]=2)=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

2°) A solution of 0.19 g of N-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine-2-carboxamide hydrobromide (1:1) in 9 mL of acetonitrile is treated with 0.5 mL of hydrochloric acid and 1 g of polymer-supported benzeneboronic acid (Alfa-Aesar L19459, ˜3 mmol/g). The reaction mixture is stirred for 16 hours at 25° C. and then refluxed for 1 hour. The resin is filtered off, washed with acetonitrile and then with methanol and the combined filtrates are evaporated to dryness under reduced pressure to give 160 mg of 2-phenylcarbamoylimidazo[1,2-a]pyridine-6-boronic acid hydrochloride (1:1) in the form of an orange-coloured solid.

Workup

temperaturerefluxed for 1 hour
filtrationThe resin is filtered off
washwashed with acetonitrile
customwith methanol and the combined filtrates are evaporated to dryness under reduced pressure

Sources & evidence

ORD record: ord-77de0fd9895a455ea591434fee7c0322
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691990B2

Reaction notes

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