6-(Dimethylamino)pyridine-3-boronic acid → 2-Tert-butoxy-2-(1-(4-chlorophenyl)-4-(6-(dimethylamino)pyridin-3-yl)-3-methylnaphthalen-2-yl)acetic acid

HRID 514134Notes

Reaction equation

HRID 514134 reaction equation
[C:1]([O:5][CH:6]([C:12]1[C:21]([CH3:22])=[C:20](C)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:31][N:32]([C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][N:35]=1)[CH3:33]>>[C:1]([O:5][CH:6]([C:12]1[C:21]([CH3:22])=[C:20]([C:37]2[CH:36]=[N:35][C:34]([N:32]([CH3:33])[CH3:31])=[CH:39][CH:38]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 27632716-(Dimethylamino)pyridine-3-boronic acidHCID 67126302Ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3,4-dimethylnaphthalen-2-yl)acetate

Product 1

HCID 680857632-Tert-butoxy-2-(1-(4-chlorophenyl)-4-(6-(dimethylamino)pyridin-3-yl)-3-methylnaphthalen-2-yl)acetic acid

Procedure

2-tert-Butoxy-2-(1-(4-chlorophenyl)-4-(6-(dimethylamino)pyridin-3-yl)-3-methylnaphthalen-2-yl)acetic acid (137) was prepared in a manner similar to 2-tert-butoxy-2-(1-(4-chlorophenyl)-3,4-dimethylnaphthalen-2-yl)acetic acid of Example 125, except using 2-(N,N-dimethylamino)-pyridin-5-yl-boronic acid in the Suzuki reaction, giving the title compound. 1H-NMR: (400 MHz, DMSO-d6): δ 8.02-8.00 (m, 1H); 7.78 (m, broad, 1H); 7.72-7.69 (m, 1H); 7.67-7.65 (m, 1H); 7.52-7.49 (m, 1H); 7.45-7.36 (m, 4H); 7.23 (d, J=8.0 Hz, 2H); 5.11 (s, 1H); 2.29 (d, J=1.2 Hz, 3H); 0.93 (d, J=1.2 Hz, 9H). LCMS-ESI+ (m/z): [M+H]+ calcd for C30H32ClN2O3: 503.2; Found: 503.3.

Workup

  1. customin the Suzuki reaction

Sources & evidence

ORD record
ord-9556fe92fc97420abe3b8e40faa67aae
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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