2-(Tri-n-butylstannyl)thiophene → N-[4-methyl-5-(2-thienyl)-1,3-thiazol-2-yl]acetamide

HRID 1364488ノート

反応式

HRID 1364488 の反応式
IC1SC(NC(=O)C)=NC=1C.C([C:14]1[S:18][C:17]([C:19]2[S:23][C:22]([NH:24][C:25](=[O:27])[CH3:26])=[N:21][C:20]=2[CH3:28])=[CH:16][CH:15]=1)=O.C([Sn](CCCC)(CCCC)C1SC=CC=1)CCC>CN(C=O)C.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]>[CH3:28][C:20]1[N:21]=[C:22]([NH:24][C:25](=[O:27])[CH3:26])[S:23][C:19]=1[C:17]1[S:18][CH:14]=[CH:15][CH:16]=1

参加物

6

反応物 3

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 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 11993489N-[4-methyl-5-(2-thienyl)-1,3-thiazol-2-yl]acetamide

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

N-(5-iodo-4-methyl-1,3-thiazol-2-yl)acetamide, Intermediate 1 (2 g; 7.09 mmol; 1 eq.) and Pd(dppf)Cl2 (0.52 g; 0.71 mmol; 0.10 eq.) are dissolved in DMF (35 ml). 2-(Tributylstannyl)thiophene (2.68 ml; 8.44 mmol; 1.19 eq.) is added. The reaction mixture is flushed with argon and heated at 100° C. for 1 h30. Solvents are evaporated and the crude mixture is dissolved in EtOAc (100 ml), washed with water (3×100 ml). The aqueous phase are combined and extracted with EtOAc (2×50 ml). Combined organic phases is washed with brine and dried over MgSO4. After evaporation of the solvents, the crude product is purified by preparative HPLC, affording Compound (6) as white-off powder (1.24 g; 73.5%). 1H NMR (DMSO-d6) δ 2.16 (s, 3H), 2.42 (s, 3H), 7.15 (dd, J=3.8, 5.3 Hz, 1H), 7.20 (dd, J=1.1, 3.8 Hz, 1H), 7.60 (dd, J=1.1, 5.3 Hz, 1H), 12.19 (s, 1H). M−(ESI): 237.01; M+(ESI): 239.01. HPLC, Rt: 3.01 min (purity: 98.7%).

後処理

  1. customThe reaction mixture is flushed with argon
  2. customSolvents are evaporated
  3. dissolutionthe crude mixture is dissolved in EtOAc (100 ml)
  4. washwashed with water (3×100 ml)
  5. extractionextracted with EtOAc (2×50 ml)
  6. washCombined organic phases is washed with brine
  7. dry with materialdried over MgSO4
  8. customAfter evaporation of the solvents
  9. customthe crude product is purified by preparative HPLC

出典と根拠

ORDレコード
ord-a88ee0da510843f4941c9c020ff5664a
出典データセット
uspto-grants-2011_02
特許番号
US07888379B2

反応ノート

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