Methylboronic Acid → HCID 66823409, compound

HRID 2362188Notes

Reaction equation

[C:1]([O:5][C:6](=[O:42])[NH:7][C:8]1([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:24][N:23]4[N:32]=[C:33]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[C:34](Br)=[C:22]4[N:21]=3)=[CH:16][CH:15]=2)[CH2:11][C:10]([OH:13])([CH3:12])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:43]B(O)O>O1CCOCC1.C(Cl)Cl.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[C:1]([O:5][C:6](=[O:42])[NH:7][C:8]1([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:24][N:23]4[N:32]=[C:33]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[C:34]([CH3:43])=[C:22]4[N:21]=3)=[CH:16][CH:15]=2)[CH2:11][C:10]([OH:13])([CH3:12])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of compound 10-3 (62 mg, 0.1 mmol), Methyl boronic acid (60 mg, 1 mmol), aq.Na2 CO3 (2M, 0.25 mmol, 0.12 mL) and Pd(DPPF)Cl2 (10 mg) in dioxane (2 mL) was heated at 100° C. in microwave system under N2 atmosphere for 30 min. After cooling, the mixture was diluted with 15 mL of DCM, the combined organic phase was washed with 0.1N HClaq and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep.TLC to give 23 mg of 10-5.

Workup

temperatureAfter cooling
washthe combined organic phase was washed with 0.1N HClaq and brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated
customThe residue was purified by prep.TLC

Sources & evidence

ORD record: ord-e0e1dd7591c1410fbb4cb779b2a38711
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691825B2

Reaction notes

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