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

HRID 916766노트

반응식

HRID 916766 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b9c4470565fb46849f2ba0a6a73d11af
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07271262B2

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