4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 56645464, compound

HRID 931817Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:10]1[C:11]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15](C1NN=CC=1)[CH:14]=[CH:13]2)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].CC1(C)C(C)(C)OB([C:41]2[CH:42]=[N:43][NH:44][CH:45]=2)O1>>[C:1]([O:5][C@@H:6]([C:10]1[C:11]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([C:41]1[CH:42]=[N:43][NH:44][CH:45]=1)[CH:14]=[CH:13]2)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HCID 66634233HCID 66634233, compound

Product 1

HCID 56645464HCID 56645464, compound

Procedure

(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(1H-pyrazol-4-yl)quinolin-6-yl)acetic acid (77) was prepared following the procedure for (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(1H-pyrazol-5-yl)quinolin-6-yl)acetic acid of Example 70 except that 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole was used instead of 1H-pyrazol-5-ylboronic acid and the in the final step the reaction was stirred for 1 hour. 1H-NMR: 400 MHz, (CD3CN) δ: 8.45 (s, 2 H), 8.08 (s, 1 H), 7.89 (d, J=8.8 Hz, 1 H), 7.73 9 (d, J=8.8 Hz, 1 H), 7.59 (m, 3 H), 7.34 (d, J=7.2 Hz, 1H), 5.22 (s, 1 H), 2.63 (s, 3 H), 0.97 (s, 9 H). LCMS-ESI+ (m/z): [M+H]+ calcd for C25H25ClN3O3: 450.15. found: 450.53.

Sources & evidence

ORD record: ord-2e18f9c2f1f543ca8fb41104759a3bdb
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

Loading…