Water → HCID 68675381, compound

HRID 2233364Notes

Reaction equation

HRID 2233364 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([C:11]([OH:13])=O)[CH:8]=[C:7]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:5]=2[CH:6]=1.N[C:24]1[CH:29]=[CH:28][C:27]([C:30]([O:32][CH3:33])=[O:31])=[CH:26][N:25]=1.P(Cl)(Cl)(Cl)=O.O.N1C=CC=C[CH:41]=1>>[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([C:11](=[O:13])[NH:25][C:24]3[CH:41]=[CH:26][C:27]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:29]=3)[CH:8]=[C:7]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:5]=2[CH:6]=1

Participants

6

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 737487Methyl 6-aminonicotinateHCID 67485267HCID 67485267, compound

Product 1

HCID 68675381HCID 68675381, compoundYield 70%

Procedure

A solution of 2-methyl-4-(2-fluorobenzyloxy)-1-benzofuran-6-carboxylic acid (Method 3; 0.60 mg, 0.2 mmol) and methyl 2-aminopyridine-5-carboxylate (61 mg, 0.4 mmol, 2 eq) in pyridine (1 ml) was treated with phosphorus oxychloride (20.5 μl, 0.22 mmol, 1.1 eq), and the reaction mixture stirred for 16 hrs at ambient temperature. The reaction mixture was poured into water and extracted twice with ethyl acetate; the extracts were washed with brine, dried (MgSO4) and evaporated to give a yellow gum. This was chromatographed (10 g Bondelut, eluting with hexane containing ethyl acetate, 0-100%) to give the title compound as a solid (61 mg, 70%). NMR: 2.46 (s, 3H), 3.87 (s, 3H), 5.37 (s, 2H), 6.66 (s, 1H), 7.25 (m, 2H), 7.42 (m, 1H), 7.62 (m, 2H), 7.91 (s, 1H), 8.36 (m, 2H), 8.91 (s, 1H), 11.20 (bs, 1H); m/z 435 (M+H)+, 100% by LC-MS.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washthe extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a yellow gum
  6. customThis was chromatographed
  7. wash(10 g Bondelut, eluting with hexane containing ethyl acetate, 0-100%)

Sources & evidence

ORD record
ord-c59bcb16db0d4b65a5b995150c6e72f3
Source dataset
uspto-grants-2010_05
Patent number
US07709505B2

Reaction notes

Loading…