(3,4,5-Trifluorophenyl)boronic Acid (contains varying amounts of Anhydride) → HCID 178462235, compound

HRID 912952Notes

Reaction equation

HRID 912952 reaction equation
Br[C:2]1[C:10]2[N:9]=[C:8]([N:11]3[CH2:16][CH2:15][N:14]([C:17]4[N:22]=[CH:21][C:20]([C@@H:23]([OH:25])[CH3:24])=[CH:19][C:18]=4[Cl:26])[CH2:13][C@H:12]3[CH3:27])[NH:7][C:6]=2[CH:5]=[C:4]([C:28]([F:31])([F:30])[F:29])[CH:3]=1.BrC1C2N=C(N3CCN(C4N=CC([C@H](O)C)=CC=4Cl)C[C@H]3C)NC=2C=C(C(F)(F)F)C=1.[F:63][C:64]1[CH:65]=[C:66](B(O)O)[CH:67]=[C:68]([F:71])[C:69]=1[F:70]>>[Cl:26][C:18]1[CH:19]=[C:20]([C@@H:23]([OH:25])[CH3:24])[CH:21]=[N:22][C:17]=1[N:14]1[CH2:15][CH2:16][N:11]([C:8]2[NH:9][C:10]3[C:2]([C:66]4[CH:65]=[C:64]([F:63])[C:69]([F:70])=[C:68]([F:71])[CH:67]=4)=[CH:3][C:4]([C:28]([F:31])([F:29])[F:30])=[CH:5][C:6]=3[N:7]=2)[C@H:12]([CH3:27])[CH2:13]1

Participants

4

Reactant 3

HCID 2734671(3,4,5-Trifluorophenyl)boronic Acid (contains varying amounts of Anhydride)HCID 67400300HCID 67400300, compoundHCID 67401127HCID 67401127, compound

Product 1

HCID 178462235HCID 178462235, compound

Procedure

The diastereoisomeric mixture of (1S)-1-{6-[(3R)-4-(4-bromo-6-trifluoromethyl-1H-benzoimidazol-2-yl)-3-methyl-piperazin-1-yl]-5-chloro-pyridin-3-yl}-ethanol and (1R)-1-{6-[(3R)-4-(4-bromo-6-trifluoromethyl-1H-benzoimidazol-2-yl)-3-methyl-piperazin-1-yl]-5-chloro-pyridin-3-yl}-ethanol (416 mg, 0.8 mmol, Example 166a) reacted with 3,4,5-trifluorophenylboronic acid (282 mg, 1.6 mmol, Lancaster) under the conditions of Example 158 to give the title compound as a mixture of diastereoisomers. Separation of the mixture by preparative HPLC on a Chiralcel OD column, eluting with 9:1 hexane/EtOH afforded the fast running title compound. The configuration (1S) was assigned at random. (ESI, neg. ion) m/z: 570 (M−1).

Sources & evidence

ORD record
ord-d000e12360164356b8e217c3cdbb228c
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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