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

HRID 1035223Notes

Reaction equation

HRID 1035223 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 45.4%

Procedure

Using a similar protocol as described in Example 53C employing 53B (1.0 g, 3.10 mmol) and 3-chloro-4-hydroxybenzaldehyde (0.50 g, 3.19 mmol) as starting materials afforded 0.54 g (45%) of 57A as a solid. 1H NMR (500 MHz, CD3OD): δ 4.34 (m, 1H), 4.77 (m, 2H), 5.25 (m, 1H), 5.36 (m, 1H), 7.05 (d, 1H), 7.62 (m, 3H), 7.7-8.1 (m, 2H), 8.14 (d, 2H), 9.87 (s, 1H), MS (APCI+) m/z 384 [M+H]+.

Sources & evidence

ORD record
ord-529cd6dffe994cd6bb95ff777c92ee5d
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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