Dimethylformamide → Tert-butyl 5-(phthalazin-6-yl)thiazol-2-ylcarbamate

HRID 661046ノート

反応式

HRID 661046 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][N:6]=[CH:5]2.C([Sn](CCCC)(CCCC)[C:17]1[S:21][C:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[N:19][CH:18]=1)CCC.CN(C=O)C.[F-].[Cs+]>C(Cl)Cl.O.[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>[CH:8]1[C:9]2[C:4](=[CH:3][C:2]([C:17]3[S:21][C:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[N:19][CH:18]=3)=[CH:11][CH:10]=2)[CH:5]=[N:6][N:7]=1

参加物

9

反応物 4

HCID 6228DimethylformamideHCID 25953Cesium fluorideHCID 6104366-BromophthalazineHCID 2763269tert-butyl N-(5-(tributylstannyl)-1,3-thiazol-2-yl)carbamate

生成物 1

HCID 57633940Tert-butyl 5-(phthalazin-6-yl)thiazol-2-ylcarbamate収率 76%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

A glass microwave reaction vessel was charged with 6-bromophthalazine (1.0 g, 5 mmol), tert-butyl 5-(tributylstannyl)thiazol-2-ylcarbamate (4.0 g, 7 mmol), DMF (4 mL), cesium fluoride (1.0 g, 10 mmol), copper(I) iodide (0.2 g, 1.0 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.3 g, 0.2 mmol). The reaction mixture was stirred and heated at 100° C. overnight. The mixture was diluted with DCM (20 mL) and water (5 mL) and filtered through Celite. The organic solution was evaporated under reduced pressure, and the residue was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 5% to 10% MeOH in DCM to provide the title compound (1.19 g, 76%). LCMS (M+H+) 329.3 calc. for C16H16N4O2S 329.3; 1H NMR (400 MHz, CDCl3) δ ppm 9.50 (s, J=13.69 Hz 1H), 9.46 (s, 1H), 8.01 (d, J=1.37, Hz 1H), 7.92 (d, J=8.41 Hz, 1H), 7.81 (s, 1H), 7.58 (s, 1H) 1.40 (s, 9H).

後処理

  1. customA glass microwave reaction vessel
  2. filtrationfiltered through Celite
  3. customThe organic solution was evaporated under reduced pressure
  4. customchromatographed through a Redi-Sep pre-packed silica gel column (40 g)
  5. washeluting with a gradient of 5% to 10% MeOH in DCM

出典と根拠

ORDレコード
ord-798b0793590c4fb18266963564aded88
出典データセット
uspto-grants-2011_12
特許番号
US08084479B2

反応ノート

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