Potassium Phosphate, Tribasic → [2-(2,6-Dichloro-4-cyano-phenyl)-thiazolo[5,4-c]pyridin-4-yl]-carbamic acid tert-butyl ester

HRID 2366238ノート

反応式

HRID 2366238 の反応式
Br[C:2]1[C:7]2[S:8][C:9]([C:11]3[C:18]([Cl:19])=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=3[Cl:20])=[N:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[C:21](=[O:28])([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH2:22].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:24]([O:23][C:21](=[O:28])[NH:22][C:2]1[C:7]2[S:8][C:9]([C:11]3[C:18]([Cl:19])=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=3[Cl:20])=[N:10][C:6]=2[CH:5]=[CH:4][N:3]=1)([CH3:27])([CH3:26])[CH3:25]

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 77922tert-Butyl carbamateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866689964-(4-Bromothiazolo[5,4-c]pyridin-2-yl)-3,5-dichlorobenzonitrile

生成物 1

HCID 66801860[2-(2,6-Dichloro-4-cyano-phenyl)-thiazolo[5,4-c]pyridin-4-yl]-carbamic acid tert-butyl ester収率 76%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

A mixture of 4-(4-bromo-thiazolo[5,4-c]pyridin-2-yl)-3,5-dichloro-benzonitrile (0.578 g, 1.50 mmol), tert-butyl carbamate (1.76 g, 15.0 mmol), Pd2(dba)3 (0.069 g, 0.075 mmol), XantPhos (0.087 g, 0.15 mmol) and tribasic potassium phosphate (0.635 g, 3.0 mmol) in toluene (10 mL) and water (1.5 mL) was degassed with argon then heated at 80° C. for 3 hours. The reaction mixture was filtered through Celite® and washed with EtOAc. The filtrate was washed with water then brine, dried over Na2SO4 and concentrated under reduced pressure. The resultant residue was purified by silica gel flash chromatography (0-50% EtOAc in pentane) to give the desired compound as an off-white solid (0.48 g, 76% yield). 1H NMR (300 MHz, CDCl3): δ 8.35 (d, J=5.6 Hz, 1H), 7.79 (d, J=5.6 Hz, 1H), 7.75 (s, 2H), 1.56 (s, 9H).

後処理

  1. customwas degassed with argon
  2. filtrationThe reaction mixture was filtered through Celite®
  3. washwashed with EtOAc
  4. washThe filtrate was washed with water
  5. dry with materialbrine, dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant residue was purified by silica gel flash chromatography (0-50% EtOAc in pentane)

出典と根拠

ORDレコード
ord-ba70db36dca94a869b440f8832563f6d
出典データセット
uspto-grants-2014_04
特許番号
US08697708B2

反応ノート

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