ethyl 5-bromo-3-{[2-(phenoxymethyl)morpholin-4-yl]sulfonyl}-1-(phenylsulfonyl)-1H-indole-2-carboxylate → (R)-5-Bromo-3-{[2-(phenoxymethyl)morpholin-4-yl]sulfonyl}-1H-indole-2-carboxamide

HRID 227483Notes

Reaction equation

HRID 227483 reaction equation
ClC1C=C2C(=CC=1)[N:7](S(C1C=CC=CC=1)(=O)=O)C(C(OCC)=O)=C2S(N1CCOC(COC2C=CC=CC=2)C1)(=O)=O.[Br:42][C:43]1[CH:44]=[C:45]2[C:49](=[CH:50][CH:51]=1)[N:48](S(C1C=CC=CC=1)(=O)=O)[C:47]([C:61](OCC)=[O:62])=[C:46]2[S:66]([N:69]1[CH2:74][CH2:73][O:72][CH:71]([CH2:75][O:76][C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)[CH2:70]1)(=[O:68])=[O:67]>>[Br:42][C:43]1[CH:44]=[C:45]2[C:49](=[CH:50][CH:51]=1)[NH:48][C:47]([C:61]([NH2:7])=[O:62])=[C:46]2[S:66]([N:69]1[CH2:74][CH2:73][O:72][C@@H:71]([CH2:75][O:76][C:77]2[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=2)[CH2:70]1)(=[O:68])=[O:67]

Participants

3

Reactant 2

HCID 68442943ethyl 5-bromo-3-{[2-(phenoxymethyl)morpholin-4-yl]sulfonyl}-1-(phenylsulfonyl)-1H-indole-2-carboxylate2×HCID 68878207Ethyl (+/-)-5-chloro-3-{[2-(phenoxymethyl)morpholin-4-yl]sulfonyl}-1-(phenylsulfonyl)-1h-indole-2-carboxylate2×

Product 1

HCID 57756206(R)-5-Bromo-3-{[2-(phenoxymethyl)morpholin-4-yl]sulfonyl}-1H-indole-2-carboxamide

Procedure

Using the same procedures described for Example 23, replacing the product from Step A of Example 22, ethyl(±)-5-chloro-3-{[2-(phenoxymethyl)morpholin-4-yl]sulfonyl}-1-(phenylsulfonyl)-1H-indole-2-carboxylate, with ethyl(±)-5-bromo-3-{[2-(phenoxymethyl)morpholin-4-yl]sulfonyl}-1-(phenylsulfonyl)-1H-indole-2-carboxylate, the second-eluting enantiomer of ethyl 5-bromo-3-{[2-(phenoxymethyl)morpholin-4-yl]sulfonyl}-1-(phenylsulfonyl)-1H-indole-2-carboxylate was converted to the titled compound after purification by preparative reversed phase HPLC. Proton NMR for the product was consistent with the titled compound. ESI+MS: 493.85 [M+H]+.

Sources & evidence

ORD record
ord-d5e7a59f43a64dcfb57dd9f9bba8cb41
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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