4-(3-Bromo-4-methylbenzene-1-sulfonyl)morpholine → HCID 58521897, compound

HRID 2390182Notes

Reaction equation

HRID 2390182 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[CH:17])([CH3:4])([CH3:3])[CH3:2].[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)(=[O:28])=[O:27])=[CH:22][C:21]=1Br>>[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[C:17][C:21]1[CH:22]=[C:23]([S:26]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)(=[O:28])=[O:27])[CH:24]=[CH:25][C:20]=1[CH3:19])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 72133094-(3-Bromo-4-methylbenzene-1-sulfonyl)morpholineHCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2×

Product 1

HCID 58521897HCID 58521897, compoundYield 81%

Procedure

Following the general method as outlined in Intermediate 20, starting from (4-chloro-2-ethynyl-phenoxy)-acetic acid tert-butyl ester (Intermediate 3) and 1-(3-bromo-4-methylphenylsulfonyl)morpholine (Combiblocks), the title compound was obtained as a yellow sticky solid in 81% yield after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-52e7a04480a64a30b2a9efce9728535e
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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