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Methanol → N-[4-(4-chloro-5-formyl-1,3-thiazol-2-yl)pyridin-2-yl]acetamide

HRID 2282294
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HRID 2282294 반응식
Cl[C:2]1[S:3][C:4]([CH:8]=[O:9])=[C:5]([Cl:7])[N:6]=1.C[Sn](C)(C)[C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19](=[O:21])[CH3:20])[CH:13]=1.[Cl-].[Li+].CO>O1CCOCC1.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:7][C:5]1[N:6]=[C:2]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19](=[O:21])[CH3:20])[CH:13]=2)[S:3][C:4]=1[CH:8]=[O:9]
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참가 물질

8

반응물 4

HCID 887MethanolHCID 433294Lithium ChlorideHCID 14886722,4-Dichloro-1,3-thiazole-5-carboxaldehydeHCID 59529632N-(4-(trimethylstannyl)pyridin-2-yl)acetamide

생성물 1

HCID 86649613N-[4-(4-chloro-5-formyl-1,3-thiazol-2-yl)pyridin-2-yl]acetamide수율 46%

시약·촉매·용매 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 178418397HCID 178418397, 화합물촉매
HCID 312751,4-Dioxane용매

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온도
110 °C

실험 절차

2,4-Dichloro-5-thiazolecarboxaldehyde (2.50 g, 0.0137 mol), N-[4-(trimethylstannyl)pyridin-2-yl]acetamide (4.93 g, 0.0165 mol), lithium chloride (1.75 g, 0.0412 mol), copper(I) iodide (0.785 g, 0.00412 mol), tetrakis(triphenylphosphine)palladium(0) (0.794 g, 0.000687 mol) were combined in dioxane (200 mL) under an atmosphere of Argon. The solution was heated at 110° C. for 2 hr. TLC indicated complete conversion. Mixture was cooled to rt and MeOH (100 mL) was added until almost all solids dissolved. Suspension was filtered through celite and the filtrate was evaporated. Water (100 mL) was added and the solids were collected by filtration, washed with water and hexane and dried in vacuum at 40° C. to give 1.76 g of amorphous solid (46%). LCMS: (FA) ES+ 282, 284. 1H NMR (400 MHz, d6-DMSO) 10.83 (s, 1H), 10.02 (s, 1H), 8.70 (s, 1H), 8.51 (dd, J=5.20, 0.67 Hz, 1H), 7.68 (dd, J=5.20, 1.67 Hz, 1H), 2.13 (s, 3H).

후처리

  1. temperatureMixture was cooled to rt
  2. dissolutiondissolved
  3. filtrationSuspension was filtered through celite
  4. customthe filtrate was evaporated
  5. additionWater (100 mL) was added
  6. filtrationthe solids were collected by filtration
  7. washwashed with water and hexane
  8. customdried in vacuum at 40° C.

출처 및 근거

ORD 기록
ord-28cc748ce43e417cb70056b089778513
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09139589B2

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