3-Chloro-4-hydroxybenzaldehyde → 3-Chloro-4-(1-(5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde

HRID 1035250Notes

Reaction equation

HRID 1035250 reaction equation
CS([O:5][CH:6]1[CH2:9][N:8]([C:10]([C:12]2[O:13][C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[N:15][N:16]=2)=[O:11])[CH2:7]1)(=O)=O.[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1O)[CH:29]=[O:30]>>[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[O:5][CH:6]1[CH2:9][N:8]([C:10]([C:12]2[O:13][C:14]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[N:15][N:16]=2)=[O:11])[CH2:7]1)[CH:29]=[O:30]

Participants

3

Reactant 2

HCID 170223-Chloro-4-hydroxybenzaldehydeHCID 580431311-(5-(4-Methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl methanesulfonate

Product 1

HCID 580431413-Chloro-4-(1-(5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehydeYield 15%

Procedure

Using a similar protocol as described in Example 71A employing 73B and 3-chloro-4-hydroxybenzaldehyde as starting materials afforded 80 mg (15%) of 79A as a solid. 1H NMR (500 MHz, CDCl3): δ 3.89 (s, 3H), 4.43 (m, 1H), 4.74 (m, 1H), 4.85 (m, 1H), 5.21 (m, 2H), 6.75 (s, 1H), 7.02 (d, 2H), 7.79 (d, 1H), 7.97 (s, 1H), 8.11 (d, 2H), 9.89 (s, 1H).

Sources & evidence

ORD record
ord-87af5de43dd14e5593bd7ea44557c766
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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