(Pyridin-4-yl)boronic acid → (S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-6-(pyridin-3-yl)naphthalen-2-yl)acetic acid

HRID 514063Notes

Reaction equation

HRID 514063 reaction equation
[C:1]([O:5][C@@H:6]([C:10]1[C:19]([CH3:20])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15](C3C=CN=CC=3)[CH:16]=2)[C:11]=1[C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].[N:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1>>[C:1]([O:5][C@@H:6]([C:10]1[C:19]([CH3:20])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:36]3[CH:35]=[N:34][CH:39]=[CH:38][CH:37]=3)[CH:16]=2)[C:11]=1[C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C:7]([OH:9])=[O:8])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 56599325(S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-6-(pyridin-4-yl)naphthalen-2-yl)acetic acid

Product 1

HCID 56599326(S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-6-(pyridin-3-yl)naphthalen-2-yl)acetic acid

Procedure

(S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-6-(pyridin-3-yl)naphthalen-2-yl)acetic acid (54) was prepared in a similar fashion to compound 53 of Example 51 with the substitution of pyridin-3-ylboronic acid for pyridin-4-ylboronic acid in step 5. The title compound (0.024 g) was isolated as an amorphous white powder. LCMS-ESI− (m/z): [2M−H]− calcd for C56H51Cl2N2O6: 917.31; found: 917.39. 1H-NMR: 400 MHz, (CD3CN) δ: 9.08 (s, 1H); 8.74 (d, J=5.2 Hz, 1H); 8.61 (d, J=8 Hz, 1H); 8.19 (s, 1H); 7.93-7.88 (m, 1H); 7.84 (s, 1H); 7.66-7.53 (m, 4H); 7.44-7.35 (m, 2H); 5.24 (s, 1H); 2.59 (s, 3H); 0.99 (s, 9H).

Sources & evidence

ORD record
ord-b282a255ea9b4268bc10a764dc8542ac
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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