1-methyl-2-(tributylstannyl)-1H-pyrrole → HCID 11553258, 화합물

HRID 28666

반응식

HRID 28666 반응식
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]([NH:19][CH2:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)=[O:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:27][N:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[Sn](CCCC)(CCCC)CCCC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:27][N:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]([NH:19][CH2:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)=[O:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 27693971-methyl-2-(tributylstannyl)-1H-pyrroleHCID 57639717HCID 57639717, 화합물

생성물 1

HCID 11553258HCID 11553258, 화합물

시약·촉매·용매 1

HCID 178418476HCID 178418476, 화합물촉매

실험 절차

A mixture of 1-(3-bromophenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide (85 mg, 0.209 mmol), Pd(PPh3)2Cl2 (28 mg, 0.040 mmol) and Ag2O (45 mg, 0.196 mmol) was added in one portion to a flask charged with 1-methyl-2-tributylstannanyl-1H-pyrrole (0.391 g, 1.06 mmol). The flask was evacuated and backfilled with N2 (2×) then charged with anhydrous DMF (3.0 mL). After stirring at rt for 5 min the reaction mixture was heated to 90° C. under N2 for 2 d. Later, the reaction was cooled to rt and treated with 1 M aq KF (3 mL) and stirred overnight at rt. Then filtered through Celite (using MeOH to rinse the Celite) and purified by MDPS to provide the product as a white solid. MS (ES+): m/z 408.46 (100) [MH+].

후처리

  1. additionwas added in one portion to a flask
  2. customThe flask was evacuated
  3. additionthen charged with anhydrous DMF (3.0 mL)
  4. temperaturewas heated to 90° C. under N2 for 2 d
  5. temperatureLater, the reaction was cooled to rt
  6. additiontreated with 1 M aq KF (3 mL)
  7. stirringstirred overnight at rt
  8. filtrationThen filtered through Celite (
  9. washto rinse the Celite) and
  10. custompurified by MDPS

출처 및 근거

ORD 기록
ord-6be9645c11bd4801a0a39a2ece2197db
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419995B2

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