2-(Pyridin-2-yl)but-3-yn-2-ol → HCID 71622137, compound

HRID 926157Notes

Reaction equation

HRID 926157 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH3:30])[C:8]([CH:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22]CC)=[O:21])=[C:9]2[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37]([OH:41])([C:39]#[CH:40])[CH3:38]>>[C:26]([O:25][C@@H:19]([C:8]1[C:7]([CH3:30])=[CH:6][C:5]2[C:10](=[CH:11][C:2]([C:40]#[C:39][C:37]([OH:41])([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][N:31]=3)[CH3:38])=[CH:3][CH:4]=2)[C:9]=1[C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)[C:20]([OH:22])=[O:21])([CH3:29])([CH3:28])[CH3:27]

Participants

3

Reactant 2

HCID 167625022-(Pyridin-2-yl)but-3-yn-2-olHCID 67126201Ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

Product 1

HCID 71622137HCID 71622137, compound

Procedure

(2S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-7-(3-hydroxy-3-(pyridin-2-yl)but-1-ynyl)-3-methylnaphthalen-2-yl)acetic acid was prepared by the method in Example 8 from ethyl 2-(7-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate and 2-(pyridin-2-yl)but-3-yn-2-ol. 1H-NMR: 400 MHz, (CD3OD) δ: 8.61 (d, J=6 Hz, 1H), 8.22 (t, J=8 Hz, 1H), 8.05 (d, J=8 Hz, 1H), 7.78 (d, J=8 Hz, 1H), 7.66 (m, 2H), 7.57 (m, 3H), 7.47 (d, J=8 Hz, 1H), 7.35 (s, 1H), 7.30 (d, J=8 Hz, 1H), 5.16 (s, 1H), 2.61 (s, 3H), 1.87 (s, 3H), 0.98 (s, 9H). LCMS-ESI+ (m/z): [M+H]+ calcd for C32H30ClNO4: 528.2. found: 528.1.

Sources & evidence

ORD record
ord-e20e4177df184d4fa21d8ab63539f74e
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

Loading…