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Triethylamine → 1-Benzyl-2,3-dibromo-4-(2,2-dimethyl-propionyloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

HRID 642244
Notes
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Reaction equation

HRID 642244 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:24])=[C:8]2[C:14]([Br:15])=[C:13]([Br:16])[N:12]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[C:32](Cl)(=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34]>CN(C1C=CN=CC=1)C.ClCCl.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:24][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])=[C:8]2[C:14]([Br:15])=[C:13]([Br:16])[N:12]([CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:9]2=[CH:10][N:11]=1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 684285581-benzyl-2,3-dibromo-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester

Product 1

HCID 684292361-Benzyl-2,3-dibromo-4-(2,2-dimethyl-propionyloxy)-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl esterYield 85.2%

Reagents, catalysts & solvents 3

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a stirring mixture of 1-benzyl-2,3-dibromo-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid ethyl ester (492 mg, 1.08 mmol), triethylamine (300 μL, 2.16 mmol), and DMAP (13 mg, 0.11 mmol) in anhydrous dichloromethane (5 mL) was added pivaloyl chloride (160 μL, 1.30 mmol); the mixture was stirred for 1 h at room temperature before diluted with EtOAc, then washed with diluted HCl aqueous solution, saturated NaCl aqueous solution respectively; the EtOAc phase was dried over anhydrous sodium sulfate, concentrated, the residue was purified by column to give a foamy brown solid, the desired title compound (495 mg, 85%). The title compound, ESI MS (m/z): 537 (M+H+).

Workup

  1. washwashed with diluted HCl aqueous solution, saturated NaCl aqueous solution respectively
  2. dry with materialthe EtOAc phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customthe residue was purified by column
  5. customto give a foamy brown solid

Sources & evidence

ORD record
ord-542870c307504b19ab1e72a349df6dbd
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07696223B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes