1,1'-Biphenyl-4-yl-boronic acid → HCID 18341264, compound

HRID 613935Notes

Reaction equation

HRID 613935 reaction equation
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7]2[CH:11]=CO[CH:8]=2)=[CH:3][CH:2]=1.[CH2:18]([C@H:25]1[CH2:29][O:28][C:27]([CH3:31])([CH3:30])[N:26]1[C:32](=[O:40])[CH2:33][N:34]1C=C(I)C=[N:35]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(C2C=CC=CC=2)C=CC(B(O)O)=CC=1>>[CH2:18]([C@H:25]1[CH2:29][O:28][C:27]([CH3:31])([CH3:30])[N:26]1[C:32](=[O:40])[CH2:33][N:34]1[CH:8]=[C:7]([C:4]2[CH:3]=[CH:2][C:1]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:6][CH:5]=2)[CH:11]=[N:35]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 183412651-(4(S)-benzyl-2,2-dimethyl-oxazolidinyl)-2-(4-iodopyrazol-1-yl)-ethanoneHCID 183802933-(Biphenyl-4-yl)furan

Product 1

HCID 18341264HCID 18341264, compoundYield 39%

Procedure

According to the procedure described in Example 1(a) for the preparation of 3-biphenyl-4-yl-furan, 1-(4(S)-benzyl-2,2-dimethyl-oxazolidinyl)-2-(4-iodopyrazol-1-yl)-ethanone was coupled to 4-biphenylboronic acid to provide in 39% yield 1-(4(S)-benzyl-2,2-dimethyl-oxazolidinyl)-2-(4-biphenyl-4-yl-pyrazol-1-yl)-ethanone as a white solid, mp 150-1° C. 1H NMR: δ 7.83 (s, 1H), 7.68 (s, 1H), 7.62-7.52 (m, 6H), 7.47-7.28 (m, 8H), 4.83, 4.38 (AB quartet, 2H, J=15.6 Hz), 4.22-4.18 (m, 1H), 3.94 (m, 2H), 3.09 (dd, 1H, J=6.4, 13.0 Hz), 2.97 (dd, 1H, J=8.5, 13.2 Hz), 1.79 (s, 3H), 1.55 (s, 3H). Anal. Calculated for C29H29N3O2 : C, 77.14; H, 6.47; N, 9.31. Found: C, 77.04; H, 6.52; N, 9.37.

Sources & evidence

ORD record
ord-c98529f5dbbf4e528642e759f11ce099
Source dataset
uspto-grants-1999_12
Patent number
US06008243

Reaction notes

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