Tolylboronic acid → HCID 59715485, compound

HRID 1880550Notes

Reaction equation

HRID 1880550 reaction equation
B(O)(O)[C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[CH:6][CH:7]=1.Br[C:12]1[CH:17]=[CH:16][C:15]([C@H:18]([NH:23][C@H:24]([C:28]([NH:30][C:31]2([C:34]#[N:35])[CH2:33][CH2:32]2)=[O:29])[CH2:25][CH2:26][CH3:27])[C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=1>Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:34]([C:31]1([NH:30][C:28](=[O:29])[C@@H:24]([NH:23][C@@H:18]([C:15]2[CH:16]=[CH:17][C:12]([C:2]3[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=3)=[CH:13][CH:14]=2)[C:19]([F:22])([F:21])[F:20])[CH2:25][CH2:26][CH3:27])[CH2:33][CH2:32]1)#[N:35]

Participants

4

Reactant 2

HCID 79799Tolylboronic acidHCID 59715504HCID 59715504, compound

Product 1

HCID 59715485HCID 59715485, compound

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

The title compound was synthesized in similar manner to that described for N1-(1-cyanocyclopropyl)-N2-{(1S)-2,2,2-trifluoro-1-[4′-(methylsulfonyl)-1,1%-biphenyl-4-yl]ethyl}-L-norvalinamide via Suzuki cross-coupling between p-tolylboronic acid and N2-[(1S)-1-(4-bromophenyl)-2,2,2-trifluoroethyl]-N1-(1-cyanocyclopropyl)-L-norvalinamide in the presence of [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), dichloromethane complex. MS (+ESI): 430 [M+1]+

Sources & evidence

ORD record
ord-6a3c6e0d2869455fbc277e191a349560
Source dataset
uspto-grants-2012_11
Patent number
US08318748B2

Reaction notes

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