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

HRID 1035248Notes

Reaction equation

HRID 1035248 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][CH:20]=[CH:19][CH:18]=3)=[N:15][N:16]=2)=[O:11])[CH2:7]1)(=O)=O.[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1O)[CH:27]=[O:28]>>[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=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][CH:20]=[CH:19][CH:18]=3)=[N:15][N:16]=2)=[O:11])[CH2:7]1)[CH:27]=[O:28]

Participants

3

Reactant 2

HCID 170223-Chloro-4-hydroxybenzaldehydeHCID 580430991-(5-Phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl methanesulfonate

Product 1

HCID 580431283-Chloro-4-(1-(5-phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehydeYield 10%

Procedure

Using a similar protocol as described in Example 71A employing 53B and 3-chloro-4-hydroxybenzaldehyde as starting materials afforded 51 mg (10%) of 78A as a solid. 1H NMR (500 MHz, CDCl3): δ 4.44 (m, 1H), 4.75 (m, 1H), 4.87 (m, 1H), 5.22 (m, 2H), 6.75 (s, 1H), 7.53 (t, 2H), 7.61 (t, 1H), 7.80 (d, 1H), 7.98 (s, 1H), 8.18 (d, 2H), 9.90 (s, 1H).

Sources & evidence

ORD record
ord-26ead60649fa4c9889a94395de34bc0a
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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