Triethylamine → HCID 89498123, compound

HRID 588693Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[C:26](Br)=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12].C(N(CC)CC)C.[CH3:41][C:42]1([CH3:49])[C:46]([CH3:48])([CH3:47])[O:45][BH:44][O:43]1>C(#N)C.O1CCCC1.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[CH2:21][N:20]([C:23]1[N:28]=[C:27]([C:29]([O:31][CH3:32])=[O:30])[C:26]([B:44]3[O:45][C:46]([CH3:48])([CH3:47])[C:42]([CH3:49])([CH3:41])[O:43]3)=[CH:25][CH:24]=1)[CH2:19][CH2:18]2)=[O:12]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of EXAMPLE 71C (500 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane (46.8 mg) and triethylamine (0.399 mL) in acetonitrile (7 mL) and tetrahydrofuran (3.5 mL) was added 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.416 mL). The mixture was heated at 100° C. in a Biotage Initiator microwave reactor for 30 minutes, cooled, diluted with ethyl acetate, and washed with brine. The organic layer was concentrated. The residue was purified by flash chromatography, eluting with 0-17% ethyl acetate in dichloromethane to provide the title compound.

Workup

temperaturecooled
washwashed with brine
concentrationThe organic layer was concentrated
customThe residue was purified by flash chromatography
washeluting with 0-17% ethyl acetate in dichloromethane

Sources & evidence

ORD record: ord-02fce2cf9f5740f99b2aaf9b7a9a320c
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227963B2

Reaction notes

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