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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
ノート
印刷プレビュー

反応式

HRID 2377079 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8f09828f7160448b92247290058866ff
出典データセット
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07468375B2

反応ノート

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