Cesium carbonate → Tert-butyl 7-(4-(5-chloropyridin-2-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylate

HRID 1626389노트

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HRID 1626389 반응식
[C:1]([C:4]1[CH:29]=[CH:28][C:7]([O:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][CH2:15][O:16]3)=[CH:11][C:10]=2[C:26]#[N:27])=[CH:6][CH:5]=1)(=[O:3])[NH2:2].Cl[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][N:32]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([NH:2][C:1]([C:4]2[CH:5]=[CH:6][C:7]([O:8][C:9]3[CH:18]=[C:17]4[C:12]([CH:13]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:14][CH2:15][O:16]4)=[CH:11][C:10]=3[C:26]#[N:27])=[CH:28][CH:29]=2)=[O:3])=[N:32][CH:33]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 276852,5-DichloropyridineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86664391tert-Butyl 7-(4-carbamoylphenoxy)-6-cyanochroman-4-carboxylate

생성물 1

HCID 67288859Tert-butyl 7-(4-(5-chloropyridin-2-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylate수율 13%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

tert-Butyl 7-(4-carbamoylphenoxy)-6-cyanochroman-4-carboxylate (30 mg, 0.076 mmol), 2,5-dichloropyridine (12 mg, 0.084 mmol), XPHOS (7.3 mg, 0.015 mmol), palladium (II) acetate (1.7 mg, 0.0076 mmol) and cesium carbonate (62 mg, 0.19 mmol) were diluted with dioxane (600 μL) in a 1 mL vial. The reaction was purged with argon for 3 minutes, capped and heated at 80° C. for 12 hours. The reaction was cooled and loaded directly onto a biotage 25 column and eluted with 5% ethyl acetate/hexanes to 75% ethyl acetate/hexanes to yield tert-butyl 7-(4-(5-chloropyridin-2-ylcarbamoyl)phenoxy)-6-cyanochroman-4-carboxylate (5 mg, 0.0099 mmol, 13% yield).

후처리

  1. customThe reaction was purged with argon for 3 minutes
  2. customcapped
  3. temperatureThe reaction was cooled
  4. washeluted with 5% ethyl acetate/hexanes to 75% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-73182cd5232a453a982e1900512da314
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785445B2

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