3-Pyridinylboronic acid → HCID 66631619, compound

HRID 931815Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:10]1[C:11]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15](C1C=CN=CC=1)[CH:14]=[CH:13]2)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].[N:34]1[CH:39]=[CH:38][CH:37]=[C:36](B(O)O)[CH:35]=1>>[C:1]([O:5][C@@H:6]([C:10]1[C:11]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([C:36]1[CH:35]=[N:34][CH:39]=[CH:38][CH:37]=1)[CH:14]=[CH:13]2)[C:7]([OH:9])=[O:8])([CH3:3])([CH3:2])[CH3:4]

Participants

Reactant 2

HCID 27343783-Pyridinylboronic acid

HCID 66631923HCID 66631923, compound

Product 1

HCID 66631619HCID 66631619, compound

Procedure

(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(pyridin-3-yl)quinolin-6-yl)acetic acid (74) was prepared following the procedure for (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(pyridin-4-yl)quinolin-6-yl)acetic acid of Example 73 except that pyridin-3-ylboronic acid was used instead of pyridin-4-ylboronic acid. 1H-NMR: 400 MHz, (CD3CN) δ: 9.49 (s, 1 H), 8.94 (d, J=8.4 Hz, 1 H), 8.79 (s, 1 H), 7.91 (m, 2H), 7.80 (Abq, J=26.2, 8.8 Hz, 2 H), 7.58 (m, 3 H), 7.34 (m, 1 H), 5.25 (s, 1 H), 2.61 (s, 3H), 0.97 (s, 9 H). LCMS-ESI+ (m/z): [M+H]+ calcd for C27H26ClN2O3: 461.16. found: 461.00.

Sources & evidence

ORD record: ord-86998688d76b4fe4a17ac9008d08c279
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

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