Sodium Carbonate → HCID 56598977, compound

HRID 2174945Notes

Reaction equation

HRID 2174945 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5](B(O)O)=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].Br[C:16]1[CH:25]=[CH:24][C:23]2[N:22]=[CH:21][C:20]3[N:26]([CH3:40])[C:27](=[N:37][C:38]#[N:39])[N:28]([C:29]4[CH:30]=[N:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=4)[C:19]=3[C:18]=2[CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:16]2[CH:25]=[CH:24][C:23]3[N:22]=[CH:21][C:20]4[N:26]([CH3:40])[C:27](=[N:37][C:38]#[N:39])[N:28]([C:29]5[CH:30]=[N:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=5)[C:19]=4[C:18]=3[CH:17]=2)=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 53407570[6-Amino-5-(trifluoromethyl)pyridin-3-yl]boronic acidHCID 86683441HCID 86683441, compound2×

Product 1

HCID 56598977HCID 56598977, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

6-amino-5-(trifluoromethyl)pyridin-3-ylboronic acid (1.677 mmol) and palladium dichlorobis triphenylphosphine (10 mol %) were added to a solution of N-(8-bromo-1-(6-methoxypyridin-3-yl)-3-methyl-1H-imidazo[4,5-c]quinolin-2(3H)-ylidene)cyanamide (compound of step 5, 1.118 mmol) in dry DMF in an inert atmosphere. Saturated Na2CO3 (0.3 ml) was added to the reaction mixture and the resulting solution was heated at 110° C. for 3 h. The solvent was removed; the crude material was extracted in EtOAc, washed with brine and dried over anhydrous Na2SO4. The solvent was evaporated and the crude solid was purified (silica gel column, EtOAc/MeOH as eluent) to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): δ 9.20 (s, 1H), 8.66 (d, J=3 Hz, 1H), 8.38 (d, J=3 Hz, 1H), 8.22 (m, 2H), 8.06 (dd, J=9 Hz, 3 Hz, 1H), 7.55 (s, 1H), 7.19 (d, J=9 Hz, 1H), 7.03 (d, J=3 Hz, 1H), 6.79 (s, 2H), 3.99 (s, 3H), 3.84 (s, 3H); MS (m/z): 491.2 (M+1)+.

Workup

  1. customThe solvent was removed
  2. extractionthe crude material was extracted in EtOAc
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was evaporated
  6. customthe crude solid was purified (silica gel column, EtOAc/MeOH as eluent)

Sources & evidence

ORD record
ord-5223a71304454aa0b006b50bd85f824c
Source dataset
uspto-grants-2015_06
Patent number
US09062046B2

Reaction notes

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