Triethylamine → N-(2-fluoropyridin-4-yl)-5-methoxy-2-[1-(4-methoxybenzyl)-1H-indazol-3-yl]pyrimidin-4-amine

HRID 1776438Notes

Reaction equation

HRID 1776438 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:27])=[N:5][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[N:10]=2)=[N:7][CH:8]=1.[F:28][C:29]1[CH:34]=[C:33](B(O)O)[CH:32]=[CH:31][N:30]=1.C(N(CC)CC)C>ClC(Cl)Cl.CN(C)C1C=CN=CC=1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:28][C:29]1[CH:34]=[C:33]([NH:27][C:4]2[C:3]([O:2][CH3:1])=[CH:8][N:7]=[C:6]([C:9]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[N:11]([CH2:18][C:19]4[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=4)[N:10]=3)[N:5]=2)[CH:32]=[CH:31][N:30]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27833962-Fluoropyridine-4-boronic acidHCID 867324165-methoxy-2-[1-(4-methoxybenzyl)-1H-indazol-3-yl]pyrimidin-4-amine

Product 1

HCID 86732467N-(2-fluoropyridin-4-yl)-5-methoxy-2-[1-(4-methoxybenzyl)-1H-indazol-3-yl]pyrimidin-4-amine

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

100 mg of 5-methoxy-2-[1-(4-methoxybenzyl)-1H-indazol-3-yl]pyrimidin-4-amine (1-4-1, 0.277 mmol, 1. eq.), 78.0 mg of (2-fluoropyridin-4-yl)boronic acid (0.553 mmol, 2 eq.) and 205 mg of copper (II) acetate were suspended in 4 ml of trichloromethane. 154 μl of triethylamine (1.11 mmol, 4 eq.) and 16.9 mg of N,N-dimethylpyridin-4-amine (138 mmol, 0.5 eq.) were added. The reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was filtered off over Celite 545 and washed with dichloromethane. The filtrate was concentrated in vacuo. The residue was purified by flash chromatography and preparative HPLC to yield 13 mg (0.03 mmol, 10.9%) of the analytically pure target compound.

Workup

  1. filtrationThe reaction mixture was filtered off over Celite 545
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash chromatography and preparative HPLC
  5. customto yield 13 mg (0.03 mmol, 10.9%) of the analytically pure target compound

Sources & evidence

ORD record
ord-19348cd8f8cc4dc59654aec4049b2421
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

Loading…