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Lithium hexamethyldisilazane → 1h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,2,3-dibromo-1-[(4-fluorophenyl)methyl]-4-hydroxy-,ethyl ester

HRID 2377079
Notes
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Reaction equation

HRID 2377079 reaction equation
[Br:1][C:2]1[C:3]([C:34]([O:36]CC)=O)=[C:4]([CH2:16][N:17]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])S(C2C=CC(C)=CC=2)(=O)=O)[N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:6]=1[Br:7].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[Br:7][C:6]1[N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:4]2=[CH:16][N:17]=[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:34]([OH:36])=[C:3]2[C:2]=1[Br:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 2733832Lithium hexamethyldisilazaneHCID 59855815Ethyl 4,5-dibromo-1-(4-fluorobenzyl)-2-({(2-ethoxy-2-oxoethyl)[(4-methylphenyl)sulfonyl]amino}methyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 598558191h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,2,3-dibromo-1-[(4-fluorophenyl)methyl]-4-hydroxy-,ethyl esterYield 60%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

Procedure

To a stirring solution of ethyl 4,5-dibromo-1-(4-fluorobenzyl)-2-({(2-ethoxy-2-oxoethyl)[(4-methylphenyl) sulfonyl]amino}methyl)-1H-pyrrole-3-carboxylate (124.2 g, 184.3 mol) in anhydrous THF (1.0 L) was added LiHMDS (405 mL, 1.0M in THF, 0.405 mol) at −78° C. over 1 h. The mixture was quenched with aq. NH4Cl, extracted with ethyl acetate. The organic layer was dried over Na2SO4, and concentrated. The residue was purified by column chromatography with etyl acetate/hexane (1/1, v:v) to ethyl acetate/dichloromethane (9/1) to give the title product (52.0 g 60% yield). 1H NMR (DMSO-d6) δ ppm. 11.50 (s, 1H), 8.63 (s, 1H), 7.16 (d, J=7.2 Hz, 4H), 5.60 (s, 2H), 5.67 (s, 2H), 4.39 (q, J=7.1 Hz, 2H,), 1.33 (t, J=7.2 Hz, 3H). LC/MS (API-ES, M+H+): 473.0.

Workup

  1. customThe mixture was quenched with aq. NH4Cl
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography with etyl acetate/hexane (1/1, v:v) to ethyl acetate/dichloromethane (9/1)

Sources & evidence

ORD record
ord-8f09828f7160448b92247290058866ff
Source dataset
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07468375B2

Reaction notes

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