2,3-Dibromo-4-hydroxy-1-methyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester → 2,3-Dibromo-4-(2,2-dimethyl-propionyloxy)-1-methyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642250Notes

Reaction equation

HRID 642250 reaction equation
C(OC(C1C([O:24][C:25](=O)[C:26]([CH3:29])([CH3:28])[CH3:27])=C2C(C)=C(C)N(CC3C=CC=CC=3)C2=CN=1)=O)C.[CH2:31]([O:33][C:34]([C:36]1[C:37]([OH:48])=[C:38]2[C:44]([Br:45])=[C:43]([Br:46])[N:42]([CH3:47])[C:39]2=[CH:40][N:41]=1)=[O:35])[CH3:32]>>[CH2:31]([O:33][C:34]([C:36]1[C:37]([O:48][C:25](=[O:24])[C:26]([CH3:29])([CH3:28])[CH3:27])=[C:38]2[C:44]([Br:45])=[C:43]([Br:46])[N:42]([CH3:47])[C:39]2=[CH:40][N:41]=1)=[O:35])[CH3:32]

Participants

3

Reactant 2

HCID 684265352,3-Dibromo-4-hydroxy-1-methyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl esterHCID 684277091-benzyl-4-(2,2-dimethyl-propionyloxy)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 684290582,3-Dibromo-4-(2,2-dimethyl-propionyloxy)-1-methyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Procedure

Prepared in analogy to that of 1-benzyl-4-(2,2-dimethyl-propionyloxy)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester from 2,3-Dibromo-4-hydroxy-1-methyl-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester. The title product, 1H NMR (200 MHz, CDCl3): δ (ppm)=8.62 (s, 1H), 4.42 (q, 2H, J=7.0 Hz), 3.94 (s, 3H), 1.49 (s, 9H), 1.42 (t, 3H, J=7.0 Hz).

Sources & evidence

ORD record
ord-665ce5df6d9a4f35bb4b01d5022a0745
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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