Lithium diisopropylamide → methyl 2-(tert-butoxy)-2-(4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate

HRID 1473191ノート

反応式

HRID 1473191 の反応式
C([N:8]1[C:12]2[C:13](=[O:35])[N:14]([CH3:34])[C:15]([CH:24]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:25]([O:27][CH3:28])=[O:26])=[C:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[C:11]=2[CH:10]=[CH:9]1)C1C=CC=CC=1.[Li+].CC([N-]C(C)C)C>O1CCCC1>[C:30]([O:29][CH:24]([C:15]1[N:14]([CH3:34])[C:13](=[O:35])[C:12]2[NH:8][CH:9]=[CH:10][C:11]=2[C:16]=1[C:17]1[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=1)[C:25]([O:27][CH3:28])=[O:26])([CH3:33])([CH3:31])[CH3:32]

参加物

4

反応物 2

HCID 2724682Lithium diisopropylamideHCID 89462902methyl 2-(1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetate

生成物 1

HCID 89463134methyl 2-(tert-butoxy)-2-(4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate収率 63%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A 0° C. solution of methyl 2-(1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetate (400 mg, 0.811 mmol) in Tetrahydrofuran (THF) (6 mL) was slowly treated with LDA (2.0 M solution in tetrahydrofuran/heptanes/ethylbenzene) (0.811 mL, 1.623 mmol) and the mixture was allowed to stir at 0° C. for 20 min. The mixture was quenched with HCl (1M) and extracted with Ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel (0-10% Methanol/DCM) to afford methyl 2-(tert-butoxy)-2-(4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate (205 mg, 0.511 mmol, 63% yield) as a pale yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 9.46 (s, 1H), 7.50-7.46 (m, 2H), 7.45-7.38 (m, 2H), 7.21-7.19 (m, 1H), 6.10-6.05 (m, 1H), 3.84-3.82 (s, 3H), 3.73-3.71 (s, 3H), 0.96 (s, 9H); LCMS (m/z) ES+=403 (M+1).

後処理

  1. customThe mixture was quenched with HCl (1M)
  2. extractionextracted with Ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel (0-10% Methanol/DCM)

出典と根拠

ORDレコード
ord-d20fbdbeaa6f4ff8934a370997fd0892
出典データセット
uspto-grants-2015_04
特許番号
US09012642B2

反応ノート

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