Potassium Carbonate → 2-((1-(4-amino-1,3,5-triazin-2-yl)-2-methyl-1H-benzo[d]imidazol-6-yl)ethynyl)bicyclo[2.2.1]heptan-2-ol

HRID 1398697ノート

反応式

HRID 1398697 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH3:10])[N:7]([C:11]3[N:16]=[CH:15][N:14]=[C:13]([NH2:17])[N:12]=3)[C:6]=2[CH:18]=1.[C:19]([C:21]1([OH:28])[CH2:26][CH:25]2[CH2:27][CH:22]1[CH2:23][CH2:24]2)#[CH:20].C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I>[NH2:17][C:13]1[N:14]=[CH:15][N:16]=[C:11]([N:7]2[C:6]3[CH:18]=[C:2]([C:20]#[C:19][C:21]4([OH:28])[CH2:26][CH:25]5[CH2:27][CH:22]4[CH2:23][CH2:24]5)[CH:3]=[CH:4][C:5]=3[N:9]=[C:8]2[CH3:10])[N:12]=1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 143098132-Ethynylbicyclo(2.2.1)heptan-2-olHCID 681818904-(6-Bromo-2-methyl-benzoimidazol-1-yl)-[1,3,5]triazin-2-ylamine

生成物 1

HCID 681817002-((1-(4-amino-1,3,5-triazin-2-yl)-2-methyl-1H-benzo[d]imidazol-6-yl)ethynyl)bicyclo[2.2.1]heptan-2-ol収率 8%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

A mixture of 4-(6-bromo-2-methyl-1H-benzo[d]imidazol-1-yl)-1,3,5-triazin-2-amine (200 mg, 0.66 mmol) and 2-ethynylbicyclo[2.2.1]heptan-2-ol (85 mg, 1.3 mmol) in DMF (2.5 mL) was treated with palladium(II) acetate (16 mg, 0.07 mmol), DPPP (58 mg, 0.14 mmol), copper(I) iodide (5 mg, 0.04 mmol) and potassium carbonate (180 mg, 1.3 mmol), then the mixture was heated at 120° C. for 40 min under microwave irradiation. After cooling to RT, the reaction mixture was filtered and the filtrate concentrated in vacuo. Purification of the residue by silica gel column chromatography furnished the title compound (18.5 mg, yield 8%): 1H NMR: (400 MHz, MeOD) delta 1.30-1.47 (m, 4H), 1.56-1.67 (m, 1H), 1.92-2.48 (m, 5H), 2.97 (s, 3H), 7.36 (dd, J=1.6, 8.4 Hz, 1H), 7.53 (d, J=8.4 Hz, 1H), 8.50 (s, 1H), 8.60 (s, 1H); LC-MS: m/z=+361.0 (M+H)+.

後処理

  1. temperatureAfter cooling to RT
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification of the residue by silica gel column chromatography

出典と根拠

ORDレコード
ord-ce47143e6b564d6d82021c877fba44c4
出典データセット
uspto-grants-2014_12
特許番号
US08901313B2

反応ノート

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