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

HRID 1364487
ノート
印刷プレビュー

反応式

HRID 1364487 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-27b9f77766ed4159aa70e52e219e1c2f
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07888379B2

反応ノート

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