(3-Chloro-4-hydroxy-5-methoxyphenyl)boronic acid → tert-Butyl 8-[6-(3-chloro-4-hydroxy-5-methoxyphenyl)-3-(cyclopropanecarbonyl)quinolin-4-yl]-2,8-diazaspiro[4,5]decane-2-carboxylate

HRID 2271698Notes

Reaction equation

HRID 2271698 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[N:17]1[CH2:33][CH2:32][C:20]2([CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22][CH2:21]2)[CH2:19][CH2:18]1.[Cl:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[C:39]([O:42][CH3:43])[C:40]=1[OH:41]>>[Cl:34][C:35]1[CH:36]=[C:37]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])=[C:5]3[N:17]2[CH2:33][CH2:32][C:20]3([CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22][CH2:21]3)[CH2:19][CH2:18]2)[CH:38]=[C:39]([O:42][CH3:43])[C:40]=1[OH:41]

Participants

3

Reactant 2

HCID 53216587(3-Chloro-4-hydroxy-5-methoxyphenyl)boronic acidHCID 66715811tert-Butyl 8-[6-bromo-3-(cyclopropanecarbonyl)quinolin-4-yl]-2,8-diazaspiro[4,5]decane-2-carboxylate

Product 1

HCID 68091922tert-Butyl 8-[6-(3-chloro-4-hydroxy-5-methoxyphenyl)-3-(cyclopropanecarbonyl)quinolin-4-yl]-2,8-diazaspiro[4,5]decane-2-carboxylateYield 191.5%

Procedure

Following general procedure F, tert-butyl 8-[6-bromo-3-(cyclopropanecarbonyl)quinolin-4-yl]-2,8-diazaspiro[4,5]decane-2-carboxylate (50 mg, 0.097 mmol) was reacted with 3-chloro-4-hydroxy-5-methoxyphenylboronic acid (41 mg, 0.161 mmol) to afford the crude product (110 mg) as a brown oil: ESI MS m/z 593 [C33H38ClN3O5+H]+.

Sources & evidence

ORD record
ord-e86f2e394b97441eb92dba2be705abff
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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