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Cesium carbonate → 5-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-carboxylic acid

HRID 1364487
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HRID 1364487 반응식
I[C:2]1[S:6][C:5]([NH:7][C:8](=[O:10])[CH3:9])=[N:4][C:3]=1[CH3:11].C(C1SC(C2SC(NC(=O)C)=NC=2C)=CC=1)=O.OB(O)[C:31]1[S:35][C:34]([C:36]([OH:38])=[O:37])=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O.CN(C=O)C>[C:8]([NH:7][C:5]1[S:6][C:2]([C:31]2[S:35][C:34]([C:36]([OH:38])=[O:37])=[CH:33][CH:32]=2)=[C:3]([CH3:11])[N:4]=1)(=[O:10])[CH3:9]
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8

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HCID 10796Cesium carbonateHCID 27798075-Boronothiophene-2-carboxylic acidHCID 11993393Acetamide, N-[5-(5-formyl-2-thienyl)-4-methyl-2-thiazolyl]-HCID 57417074N-(5-Iodo-4-methyl-2-thiazolyl)acetamide

생성물 1

HCID 119933965-[2-(Acetylamino)-4-methyl-1,3-thiazol-5-yl]thiophene-2-carboxylic acid

시약·촉매·용매 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 962Water용매
HCID 6228Dimethylformamide용매

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온도
150 °C

실험 절차

N-(5-iodo-4-methyl-1,3-thiazol-2-yl)acetamide, Intermediate 1 (550 mg; 1.95 mmol; 1 eq.), 5-(dihydroxyboryl)-2-thiophenecarboxylic acid (335.3 mg; 1.95 mmol; 1 eq.), cesium carbonate (1397.5 mg; 4.29 mmol; 2.20 eq.), Pd(dppf)Cl2 (57.1 mg; 0.08 mmol; 0.04 eq.) are put in a microwave reactor, followed by DMF (8 ml) and water (4 ml). The reaction mixture is flushed with argon and is heated under microwave action for 10 min at 150° C. It is filtered through a paper filter, diluted with HCl 1N solution (10 ml) and the desired product is extracted with EtOAc. Combined organic layer is dried over MgSO4, filtered and evaporated. The crude product is purified by preparative HPLC, affording Compound (4) as white-off solid (125 mg; 22.7%). 1H NMR (DMSO-d6) δ 2.14 (s, 3H), 2.44 (s, 3H), 7.21 (d, J=3.8 Hz, 1H), 7.67 (d, J=3.8 Hz, 1H), 12.30 (s, 1H), 13.15 (br s, 1H). M−(ESI): 281; M+(ESI): 283. HPLC, Rt: 2.54 min (purity: 99.9%).

후처리

  1. customThe reaction mixture is flushed with argon
  2. filtrationIt is filtered through a paper
  3. filtrationfilter
  4. additiondiluted with HCl 1N solution (10 ml)
  5. extractionthe desired product is extracted with EtOAc
  6. dry with materialCombined organic layer is dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product is purified by preparative HPLC

출처 및 근거

ORD 기록
ord-27b9f77766ed4159aa70e52e219e1c2f
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07888379B2

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