Diisopropylethylamine → 6-phenoxy-N-[[2-(trifluoromethyl)-1H-indol-5-yl]methyl]pyridine-3-carboxamide

HRID 388392Notes

Reaction equation

HRID 388392 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]1([O:31][C:32]2[N:37]=[CH:36][C:35]([C:38]([OH:40])=O)=[CH:34][CH:33]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CCN(C(C)C)C(C)C.[F:50][C:51]([F:64])([F:63])[C:52]1[NH:53][C:54]2[C:59]([CH:60]=1)=[CH:58][C:57]([CH2:61][NH2:62])=[CH:56][CH:55]=2>CN(C=O)C>[O:31]([C:32]1[N:37]=[CH:36][C:35]([C:38]([NH:62][CH2:61][C:57]2[CH:58]=[C:59]3[C:54](=[CH:55][CH:56]=2)[NH:53][C:52]([C:51]([F:64])([F:50])[F:63])=[CH:60]3)=[O:40])=[CH:34][CH:33]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27764976-Phenoxynicotinic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58126817(2-(Trifluoromethyl)-1h-indol-5-yl)methanamine2×

Product 1

HCID 444664536-phenoxy-N-[[2-(trifluoromethyl)-1H-indol-5-yl]methyl]pyridine-3-carboxamideYield 16.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred solution of HATU (121 mg, 0.319 mmol) in DMF (1 ml) was added 6-(phenyloxy)-3-pyridinecarboxylic acid (Maybridge; 51.5 mg, 0.239 mmol) in DMF (0.5 ml), followed by DIPEA (0.084 ml, 0.479 mmol) and finally {[2-(trifluoromethyl)-1H-indol-5-yl]methyl}amine (Intermediate 4, 40 mg, 0.160 mmol) in DMF (1 ml). The solution was stirred for 24 hrs. DMF was removed using a rotary evaporator followed by addition of DCM and sodium bicarbonate solution. The mixture was poured through a phase separation cartridge, the organic layer evaporated to dryness and purified using MDAP to give the title compound as a white solid (11 mg);

Workup

  1. customDMF was removed
  2. customa rotary evaporator
  3. additionfollowed by addition of DCM and sodium bicarbonate solution
  4. additionThe mixture was poured through a phase separation cartridge
  5. customthe organic layer evaporated to dryness
  6. custompurified

Sources & evidence

ORD record
ord-94284cbfca864e8f8ba17e515eb950ea
Source dataset
uspto-grants-2013_02
Patent number
US08377941B2

Reaction notes

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