Sodium Carbonate → HCID 89906627, compound

HRID 629113Notes

Reaction equation

HRID 629113 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][N:22]=1)[C:17]([OH:19])=O.[F:23][C:24]([F:34])([F:33])[O:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.C([O-])([O-])=O.[Na+].[Na+]>CC#N>[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][N:22]=1)[C:17]([NH:30][C:29]1[CH:31]=[CH:32][C:26]([O:25][C:24]([F:23])([F:33])[F:34])=[CH:27][CH:28]=1)=[O:19]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 2227012-Bromoisonicotinic acidHCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 89906627HCID 89906627, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Carbonyldiimidazole (2.367 g, 14.60 mmol) was added to a stirred solution of 2-bromoisonicotinic acid (2.4572 g, 12.16 mmol) in MeCN (30 mL) and the RM was stirred at RT for 3 h. 4-(trifluoromethoxy)aniline (2.467 mL, 18.25 mmol) was added and RM was stirred at RT overnight. and the mixture was treated with sat. aq. Na2CO3 (50 mL) and extracted with TBME. The combined extracts were washed with aq. HCl (pH=3), brine, dried over MgSO4 and the solvent was evaporated off under reduced pressure to a residue which was triturated with n-heptane and filtered to yield the title compound as a white solid. UPLC-MS (Condition 1) tR=1.55 min, m/z=360.9-362.9 [M+H]+, m/z=358.9-360.9 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm: 7.40 (d, J=8.56 Hz, 2H) 7.77-7.97 (m, 3H) 8.12 (s, 1H) 8.61 (d, J=5.14 Hz, 1H) 10.72 (s, 1H).

Workup

  1. stirringRM was stirred at RT overnight
  2. extractionextracted with TBME
  3. washThe combined extracts were washed with aq. HCl (pH=3), brine
  4. dry with materialdried over MgSO4
  5. customthe solvent was evaporated off under reduced pressure to a residue which
  6. customwas triturated with n-heptane
  7. filtrationfiltered

Sources & evidence

ORD record
ord-821251def376417f8b006e50c9c86727
Source dataset
uspto-grants-2016_04
Patent number
US09315489B2

Reaction notes

Loading…