2-(1-(3,4-difluorophenylsulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetic acid → [1-(3-Fluoro-4-morpholin-4-yl-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid

HRID 1445663Notes

Reaction equation

HRID 1445663 reaction equation
C([C:3]1[CH:4]=[C:5]([S:15]([N:18]2[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[C:20]([CH2:27][C:28]([OH:30])=[O:29])=[C:19]2[CH3:31])(=[O:17])=[O:16])[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)#N.[F:32]C1C=C(S(N2C3=NC=CC=C3C(CC(O)=O)=C2C)(=O)=O)C=CC=1F>>[F:32][C:3]1[CH:4]=[C:5]([S:15]([N:18]2[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[C:20]([CH2:27][C:28]([OH:30])=[O:29])=[C:19]2[CH3:31])(=[O:16])=[O:17])[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 116677412-(1-(3,4-difluorophenylsulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetic acidHCID 23582407[1-(3-Cyano-4-morpholin-4-yl-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid2×

Product 1

HCID 67219323[1-(3-Fluoro-4-morpholin-4-yl-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid

Procedure

The titled compound is prepared analogously to [1-(3-cyano-4-morpholin-4-yl-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester (Intermediate 151b) by replacing [1-(3-cyano-4-fluoro-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester with [1-(3,4-difluoro-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid (Example 59) and by heating using microwave radiation in a Personal Chemistry Emrys™ Optimizer microwave reactor at 60-80° C. for 4 hours. (MH+ 434)

Workup

  1. temperatureby heating
  2. customat 60-80° C.
  3. customfor 4 hours

Sources & evidence

ORD record
ord-3fd4224c414f445e89c3bd6c7865698f
Source dataset
uspto-grants-2010_02
Patent number
US07666878B2

Reaction notes

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