Sodium Bicarbonate → HCID 135900033, compound

HRID 423152Notes

Reaction equation

HRID 423152 reaction equation
Cl.C([O:4][C:5](=O)[CH:6]([C:20]1[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][C:21]=1[N+:28]([O-])=[O:29])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:9][N:8]=1)C.C(=O)([O-])O.[Na+].[NH4+]=S>C1(C)C=CC=CC=1.O>[OH:29][N:28]1[C:21]2[C:20](=[CH:25][C:24]([C:26]#[N:27])=[CH:23][CH:22]=2)[C:6]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[CH:9][N:8]=2)=[C:5]1[OH:4]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 66674206HCID 66674206, compound

Product 1

HCID 135900033HCID 135900033, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

(5-Cyano-2-nitro-phenyl)-(5-morpholin-4-ylmethyl-pyridin-2-yl)-acetic acid ethyl ester HCl (8.0 g, 17.9 mmol was slurried in toluene (80 ml) at room temperature and sodium hydrogen carbonate (7.52 g, 89.5 μmol) dissolved in water (50 ml) was added and the reaction mixture stirred at room temperature for 25 min. The organic phase was separated and washed with water and then concentrated to dryness and then redissolved in ethanol (80 ml) and the solution added to a preheated solution of ammonium sulphide (26 ml, 21 w/w %, 107.4 mmol) in water at 50° C. over 20 mins. The resulting yellow slurry was stirred for 1 hr at 50° C. then cooled in an ice bath. The slurry was filtered and washed with water followed by isopropanol. After drying at 50° C. under vacuum gave a yellow powder, 6.67 g, (purity 94%), 76% yield of 1,2-Dihydroxy-3-(5-morpholin-4-ylmethyl-pyridin-2-yl)-1H-indole-5-carbonitrile. 1H NMR (400 MHz; d6-DMSO,): δ 14.36 (br s, 1H), 10.86 (br s, 1H), 8.12 (s, 1H), 7.96 (s, 1H), 7.88 (br d, 1H), 7.87 (br d, 1H), 7.78 (br dd, 1H), 7.36 (dd, J=1.0, 8.0 Hz, 1H), 7.08 (d, H=8.1 Hz, 1H), 3.56 (t, J=4.0, 8.2 Hz, 4H), 3.37 (s, 2H), 2.27 (br s, 4H); 13C NMR: (100 MHz, d6-DMSO): δ 163.8, 148.8, 142.7, 136.7, 136.1, 123.1, 121.5, 120.4, 119.4, 119.1, 102.0, 81.9, 67.2, 66.6, 58.8, 53.3 ppm; MS (ESI) m/z [M+1]+ 351.

Workup

  1. additionwas added
  2. customThe organic phase was separated
  3. washwashed with water
  4. concentrationconcentrated to dryness
  5. dissolutionredissolved in ethanol (80 ml)
  6. stirringThe resulting yellow slurry was stirred for 1 hr at 50° C.
  7. temperaturethen cooled in an ice bath
  8. filtrationThe slurry was filtered
  9. washwashed with water
  10. customAfter drying at 50° C. under vacuum

Sources & evidence

ORD record
ord-92f4ce2f4add4456a50f16b7a3fe215f
Source dataset
uspto-grants-2012_01
Patent number
US08101750B2

Reaction notes

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