Tert-butyl 4-(4-amino-7-iodothieno[3,2-c]pyridin-3-yl)phenylcarbamate → Tert-butyl 4-(4-amino-7-pyridin-2-ylthieno[3,2-c]pyridin-3-yl)phenylcarbamate

HRID 2390658ノート

反応式

HRID 2390658 の反応式
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[C:5](I)=[CH:4][N:3]=1>COCCOC.[Cu]I>[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:4][N:3]=1

参加物

4

反応物 1

HCID 18451463Tert-butyl 4-(4-amino-7-iodothieno[3,2-c]pyridin-3-yl)phenylcarbamate

生成物 1

HCID 18451464Tert-butyl 4-(4-amino-7-pyridin-2-ylthieno[3,2-c]pyridin-3-yl)phenylcarbamate収率 66.3%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

A suspension of Example 77A (734 mg, 1.6 mmol) and pyridyl-2-trimethylstannane (418 mg, 1.72 mmol) in DME (12 mL) was degassed with nitrogen, and PdCl2(o-tol3P)2 (62 mg, 0.078 mmol) and CuI (15 mg, 0.078 mmol) were added. The reaction vessel was sealed and the reaction was heated to 90° C. for 16 h. After cooling, the mixture was partitioned between EtOAc and H2O. The extracts were dried (Na2SO4) and concentrated, and the residue was purified by flash chromatography on silica gel, eluting with 40-75% EtOAc/hexanes to give the desired product (222 mg). MS (ESI(+)) m/e 419.0 (M+H)+.

後処理

  1. additionwere added
  2. customThe reaction vessel was sealed
  3. temperatureAfter cooling
  4. customthe mixture was partitioned between EtOAc and H2O
  5. dry with materialThe extracts were dried (Na2SO4)
  6. concentrationconcentrated
  7. customthe residue was purified by flash chromatography on silica gel
  8. washeluting with 40-75% EtOAc/hexanes

出典と根拠

ORDレコード
ord-8e596524caaf495a80c7ff866154b17e
出典データセット
uspto-grants-2012_09
特許番号
US08273736B2

反応ノート

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