3-Iodo-N-methoxy-N-methylbenzamide → (4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-iodo-phenyl)-methanone

HRID 916766ノート

反応式

HRID 916766 の反応式
[Li]CCCC.Br[C:7]1[C:15]2[C:14]([Cl:16])=[N:13][CH:12]=[N:11][C:10]=2[N:9]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:8]=1.[I:22][C:23]1[CH:24]=[C:25]([CH:32]=[CH:33][CH:34]=1)[C:26](N(OC)C)=[O:27]>C1COCC1>[Cl:16][C:14]1[C:15]2[C:7]([C:26]([C:25]3[CH:32]=[CH:33][CH:34]=[C:23]([I:22])[CH:24]=3)=[O:27])=[CH:8][N:9]([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[C:10]=2[N:11]=[CH:12][N:13]=1

参加物

5

反応物 3

HCID 223220523-Iodo-N-methoxy-N-methylbenzamideHCID 865964995-Bromo-4-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidineHCID 178418339Butyllithium

生成物 1

HCID 86760548(4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-iodo-phenyl)-methanone収率 49.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

n-BuLi (3.65 mL, 2.5 M in hexanes, 9.14 mmol) was added dropwise to a solution of 5-Bromo-4-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine (2.5 g, 8.31 mmol) in THF (50 mL) at −78° C. After 30 min a solution of 3-Iodo-N-methoxy-N-methyl-benzamide (2.29 g, 7.8 mmol) in THF (10 mL) was added. After 30 min the reaction was quenched with water and allowed to warm to room temperature. The layers were separated and the aqueous layer was extracted with EtOAc (2×). The combined organic layers were washed with water and dried over Na2SO4. Recrystallization from MeOH afforded the title compound as a white solid (1.74 g, 49%). MS: 451.9/453.9 (MH+); HPLC Rf: 7.44 min. (HPLC method 4).

後処理

  1. customAfter 30 min the reaction was quenched with water
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over Na2SO4
  6. customRecrystallization from MeOH

出典と根拠

ORDレコード
ord-b9c4470565fb46849f2ba0a6a73d11af
出典データセット
uspto-grants-2007_09
特許番号
US07271262B2

反応ノート

読み込み中…