2-(Tributylstannyl)pyridine → HCID 56599726, compound

HRID 514069Notes

Reaction equation

HRID 514069 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]([C:21]3[CH:26]=CC=[CH:23][N:22]=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].C([Sn](CCCC)(CCCC)[C:39]1C=CC=C[N:40]=1)CCC>>[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:21]3[N:22]=[CH:23][N:40]([CH3:39])[CH:26]=3)[CH:16]=2)[C:11]=1[C:27]1[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 56599532HCID 56599532, compound

Product 1

HCID 56599726HCID 56599726, compound

Procedure

(S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-6-(1-methyl-1H-imidazol-4-yl)naphthalen-2-yl)acetic acid (64) was prepared in a similar fashion to compound 63 with the substitution of 1-methyl-4-(tributylstannyl)-1H-imidazole for 2-(tributylstannyl)pyridine in step 1. The title compound (0.026 g) was isolated as an amorphous white powder. LCMS-ESI+ (m/z): [M+H]+ calcd for C27H28ClN2O3: 463.98; found: 463.86. 1H-NMR: 400 MHz, (CD3CN) δ: 6.46 (br s, 1H); 8.24 (br s, 1H); 7.73 (br s, 1H); 7.65 (s, 1H); 7.62-7.51 (m, 4H); 7.36-7.25 (m, 2H); 5.21 (s, 1H): 3.85 (s, 3H); 2.56 (s, 3H); 0.97 (s, 9H).

Sources & evidence

ORD record
ord-1b36e66a5cec41c885079176fb3d0c08
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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