Sodium Bicarbonate → 6-((5-chloro-3H-imidazo[4,5-b]pyridin-3-yl)methyl)quinoline

HRID 1404775Notes

Reaction equation

HRID 1404775 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)[C:5]([NH2:20])=[CH:4][CH:3]=1.[C:21](=O)(O)[O-].[Na+]>C(O)=O>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:9][C:10]3[CH:11]=[C:12]4[C:17](=[CH:18][CH:19]=3)[N:16]=[CH:15][CH:14]=[CH:13]4)[CH:21]=[N:20][C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 866980786-chloro-N2-(quinolin-6-ylmethyl)pyridine-2,3-diamine

Product 1

HCID 585147786-((5-chloro-3H-imidazo[4,5-b]pyridin-3-yl)methyl)quinolineYield 97%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
300 °C

Procedure

Intermediate 9 (0.200 g, 0.702 mmol) was dissolved in formic acid (1.0 ml) and heated to 300° C. and stirred for 12 h. The reaction mixture was poured into ice water and pH adjusted to 7-8 with sodium bicarbonate solution, extracted with ethyl acetate, washed with brine, dried over sodium sulphate and concentrated to afford the title compound as yellowish brown solid (0.200 g, 97% yield). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ8.88 (dd, J=4.0, 1.3 Hz, 1H), 8.70 (s, 1H), 8.33 (d, J=8.2 Hz, 1H), 8.19 (d, J=8.3 Hz, 1H), 8.01 (d, J=8.8 Hz, 1H), 7.81 (s, 1H), 7.73 (dd, J=8.7, 1.7 Hz, 1H), 7.52 (dd, J=8.3, 2.2 Hz, 1H), 7.37 (d, J=8.4 Hz, 1H), 5.69 (s, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-94001df5070f4541934284950c068baf
Source dataset
uspto-grants-2014_12
Patent number
US08912331B2

Reaction notes

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